Carbon C-13

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 10 g of butylbromide, 6.36 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo leaving 5.15 g of product estimated at 49.3% yield. Gas chromatography showed the product to be N-butyl morpholine in approximately 95% purity. Combined 7.2 g of N-butyl morpholine together with 3.0 ml of chloroacetonitrile in a small vial. After capping the vial was heated to 60° C. for approximately 24 hours. An oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. An oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 10 g of butylbromide, 6.36 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo leaving 5.15 g of product estimated at 49.3% yield. Gas chromatography showed the product to be N-butyl morpholine in approximately 95% purity. Combined 7.2 g of N-butyl morpholine together with 3.0 ml of chloroacetonitrile in a small vial. After capping the vial was heated to 60° C. for approximately 24 hours. An oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. An oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250 mL 2-neck flask was charged with 20.6 g (0.10 mol) of 4-tert-octylphenol obtained from Aldrich Chemical Co., a catalytic amount of dry, ground potassium carbonate (1.38 g, 0.010 mol) obtained from EM Science, Inc., a stir bar, and 95%. ethanol (70 mL) under argon. The side arm was then stoppered, and a condenser with an argon inlet was attached to the center neck. Stirring was commenced to dissolve the phenol, then cold propylene oxide (8.4 mL, 7.0 g, 0.12 mol) obtained from Aldrich Chemical Co. was added. The reaction was refluxed 3 hours, allowed to cool, and the ethanol was removed by rotary evaporation. The colorless oil was dissolved in 120 mL ethyl ether, and washed twice successively with 5% aqueous sodium hydroxide, followed by water. After drying over anhydrous MgSO4, the ether was evaporated off to give 25.3 g of crude product, which contained about 22 mol % unreacted phenol, and about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer. The product was purified by dissolving in 100 mL hexanes, and extracting with 4×50 mL 5% NaOH in 15:85 v/v water/methanol. The methanol layers were back-extracted with 50 mL hexanes obtained from EM Science, Inc. The hexanes layers were dried over anhydrous MgSO4, and the hexanes removed under vacuum to afford a combined yield of 13.3 g (50%) of material that contained less than 1% unreacted phenol. The structure of the compound was corroborated by proton (1H) and carbon-13 NMR spectrometry. Proton NMR revealed the material to contain about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250 mL 2-neck flask was charged with 20.6 g (0.10 mol) of 4-tert-octylphenol obtained from Aldrich Chemical Co., a catalytic amount of dry, ground potassium carbonate (1.38 g, 0.010 mol) obtained from EM Science, Inc., a stir bar, and 95%. ethanol (70 mL) under argon. The side arm was then stoppered, and a condenser with an argon inlet was attached to the center neck. Stirring was commenced to dissolve the phenol, then cold propylene oxide (8.4 mL, 7.0 g, 0.12 mol) obtained from Aldrich Chemical Co. was added. The reaction was refluxed 3 hours, allowed to cool, and the ethanol was removed by rotary evaporation. The colorless oil was dissolved in 120 mL ethyl ether, and washed twice successively with 5% aqueous sodium hydroxide, followed by water. After drying over anhydrous MgSO4, the ether was evaporated off to give 25.3 g of crude product, which contained about 22 mol % unreacted phenol, and about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer. The product was purified by dissolving in 100 mL hexanes, and extracting with 4×50 mL 5% NaOH in 15:85 v/v water/methanol. The methanol layers were back-extracted with 50 mL hexanes obtained from EM Science, Inc. The hexanes layers were dried over anhydrous MgSO4, and the hexanes removed under vacuum to afford a combined yield of 13.3 g (50%) of material that contained less than 1% unreacted phenol. The structure of the compound was corroborated by proton (1H) and carbon-13 NMR spectrometry. Proton NMR revealed the material to contain about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 10 g of butylbromide, 6.36 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo leaving 5.15 g of product estimated at 49.3% yield. Gas chromatography showed the product to be N-butyl morpholine in approximately 95% purity. Combined 7.2 g of N-butyl morpholine together with 3.0 ml of chloroacetonitrile in a small vial. After capping the vial was heated to 60° C. for approximately 24 hours. An oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. An oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in a white solid in nearly stoichiometric yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84% . Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60° C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity. Combined were 2.3 g of N-octyl morpholine together with 1.0 g of chloroacetonitrile in a small vial. After capping the vial was heated to 55° C. for approximately 24 hours. A viscous oil resulted which solidified upon addition of a small amount of ethylacetate. The solid was filtered and washed with excess ethylacetate, then dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%. Carbon-13 NMR analysis revealed the desired product present with no other detectable impurities noted. the solid sodium carbonate filtered Acetone was removed a roto-evaporator The resulting oil was dissolved in ether washed twice with water and once with brine solution The ether solution was dried over anhydrous sodium sulfate After filtering ether was removed in-vacuo leaving a slightly-colored oil obtained with a yield of 98% was heated to 55° C. for approximately 24 hours A viscous oil resulted which The solid was filtered washed with excess ethylacetate dried in a vacuum dessicator resulting in the isolation of a white solid, in a yield of approximately 84%