2,3-dimethylbutan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Into a 500 mL flask containing a stir bar, and fitted with a condenser, was placed 180 g of anhydrous tetrahydrofuran, 40 g of 2,3-dimethyl-2-butanol and 40.93 g of triethylamine under a N2 atmosphere. To this was dropwise added 40.927 g of purified methacroyl chloride from an addition funnel. Reaction was allowed to warm moderately. After 24 hrs of stirring, the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added. The salts were then filtered off though a Buchner funnel. The ethyl acetate was then stripped by use of a rotory-evaporator. A vacuum distillation column was set up with an 8 inch Vigreaux column, stir bar and a few small boiling chips. A fractional distillation was performed and 19.8 g of the product was recovered in the fraction which had a boiling point of approximately 80-87° C. at 6-7 Torr of pressure. 1H NMR was used to confirm structure and purity. Into a 500 mL flask containing a stir bar fitted with a condenser Reaction to warm moderately the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added The salts were then filtered off though a Buchner funnel The ethyl acetate was then stripped by use of a rotory-evaporator A vacuum distillation column stir bar A fractional distillation 19.8 g of the product was recovered in the fraction which

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Into a 500 mL flask containing a stir bar, and fitted with a condenser, was placed 180 g of anhydrous tetrahydrofuran, 40 g of 2,3-dimethyl-2-butanol and 40.93 g of triethylamine under a N2 atmosphere. To this was dropwise added 40.927 g of purified methacroyl chloride from an addition funnel. Reaction was allowed to warm moderately. After 24 hrs of stirring, the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added. The salts were then filtered off though a Buchner funnel. The ethyl acetate was then stripped by use of a rotory-evaporator. A vacuum distillation column was set up with an 8 inch Vigreaux column, stir bar and a few small boiling chips. A fractional distillation was performed and 19.8 g of the product was recovered in the fraction which had a boiling point of approximately 80-87° C. at 6-7 Torr of pressure. 1H NMR was used to confirm structure and purity. Into a 500 mL flask containing a stir bar fitted with a condenser Reaction to warm moderately the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added The salts were then filtered off though a Buchner funnel The ethyl acetate was then stripped by use of a rotory-evaporator A vacuum distillation column stir bar A fractional distillation 19.8 g of the product was recovered in the fraction which

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10.22 grams (0.10 mole) of 2,3-dimethylbutan-2-ol in 75 milliliters of anhydrous tetrahydrofuran at 0° C was added one equivalent of methyllithium in diethyl ether, followed by 12.1 grams (0.10 mole) of allyl chloroformate in 25 milliliters of anhydrous tetrahydrofuran. During both additions the temperature was maintained at 0° C. After the last addition was complete the reaction mixture was stirred for about 18 hours and allowed to warm to ambient temperature. The reaction mixture was poured into water, and then extracted with ether. The ether solution was washed four times with water and dried over magnesium sulfate. Removal of solvent under reduced pressure yielded 16.45 grams (88.4% crude yield) of a light yellow oil. Distillation under vacuum provided three fractions. After the last addition to warm to ambient temperature extracted with ether The ether solution was washed four times with water dried over magnesium sulfate Removal of solvent under reduced pressure yielded 16.45 grams (88.4% crude yield) of a light yellow oil Distillation under vacuum provided three fractions

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10.22 grams (0.10 mole) of 2,3-dimethylbutan-2-ol in 75 milliliters of anhydrous tetrahydrofuran at 0° C was added one equivalent of methyllithium in diethyl ether, followed by 12.1 grams (0.10 mole) of allyl chloroformate in 25 milliliters of anhydrous tetrahydrofuran. During both additions the temperature was maintained at 0° C. After the last addition was complete the reaction mixture was stirred for about 18 hours and allowed to warm to ambient temperature. The reaction mixture was poured into water, and then extracted with ether. The ether solution was washed four times with water and dried over magnesium sulfate. Removal of solvent under reduced pressure yielded 16.45 grams (88.4% crude yield) of a light yellow oil. Distillation under vacuum provided three fractions. After the last addition to warm to ambient temperature extracted with ether The ether solution was washed four times with water dried over magnesium sulfate Removal of solvent under reduced pressure yielded 16.45 grams (88.4% crude yield) of a light yellow oil Distillation under vacuum provided three fractions

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

Procedure: Into a 500 mL flask containing a stir bar, and fitted with a condenser, was placed 180 g of anhydrous tetrahydrofuran, 40 g of 2,3-dimethyl-2-butanol and 40.93 g of triethylamine under a N2 atmosphere. To this was dropwise added 40.927 g of purified methacroyl chloride from an addition funnel. Reaction was allowed to warm moderately. After 24 hrs of stirring, the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added. The salts were then filtered off though a Buchner funnel. The ethyl acetate was then stripped by use of a rotory-evaporator. A vacuum distillation column was set up with an 8 inch Vigreaux column, stir bar and a few small boiling chips. A fractional distillation was performed and 19.8 g of the product was recovered in the fraction which had a boiling point of approximately 80-87° C. at 6-7 Torr of pressure. 1H NMR was used to confirm structure and purity. Into a 500 mL flask containing a stir bar fitted with a condenser Reaction to warm moderately the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added The salts were then filtered off though a Buchner funnel The ethyl acetate was then stripped by use of a rotory-evaporator A vacuum distillation column stir bar A fractional distillation 19.8 g of the product was recovered in the fraction which

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

Procedure: Into a 500 mL flask containing a stir bar, and fitted with a condenser, was placed 180 g of anhydrous tetrahydrofuran, 40 g of 2,3-dimethyl-2-butanol and 40.93 g of triethylamine under a N2 atmosphere. To this was dropwise added 40.927 g of purified methacroyl chloride from an addition funnel. Reaction was allowed to warm moderately. After 24 hrs of stirring, the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added. The salts were then filtered off though a Buchner funnel. The ethyl acetate was then stripped by use of a rotory-evaporator. A vacuum distillation column was set up with an 8 inch Vigreaux column, stir bar and a few small boiling chips. A fractional distillation was performed and 19.8 g of the product was recovered in the fraction which had a boiling point of approximately 80-87° C. at 6-7 Torr of pressure. 1H NMR was used to confirm structure and purity. Into a 500 mL flask containing a stir bar fitted with a condenser Reaction to warm moderately the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added The salts were then filtered off though a Buchner funnel The ethyl acetate was then stripped by use of a rotory-evaporator A vacuum distillation column stir bar A fractional distillation 19.8 g of the product was recovered in the fraction which

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

Procedure: To a solution of 8.25 g (0.15 mole) propionitrile in 25 mL glacial acetic acid, 15 g concentrated sulfuric acid was added dropwise while controlling the reaction temperature at about 38° C., then 5.2 g (0.051 mole) of 2,3-dimethyl-2-butanol was added dropwise at the temperature below 40° C. with stirring. The mixture was stirred overnight while maintaining the temperature, then poured into glacial water, basified with 40% sodium hydroxide solution and extracted with ether. The ether extract was combined, washed once with water, and dried over anhydrous magnesium sulfate. After recovering the ether, 6.2 g light yellow liquid was obtained and solved in 80 mL anhydrous ether. The resulting solution was added dropwise to a suspension of 3.04 g (0.08 mol) lithium aluminium hydride in 80 mL anhydrous ether. The mixture was refluxed for 10 hours, then cooled. To the mixture, proper amount of 40% aqueous sodium hydroxide was added dropwise and the upper layer of ether was carefully poured out. The lower layer of solid was then washed with ether (×3). The resulting washing and extract ether were combined, dried over anhydrous potassium carbonate and filtered. To the filtrate, HCl-Et2O was added under cooling until the solution is acidic. The solid was collected by filtering and recrystallized three times from iso-propanol and acetone to give a white lamellar crystal 3.33 g (yield 46.33%), mp 183-185° C. Elemental analysis for C9H22NCI (%): Calculated C, 10.15; H, 12.34; N, 7.79. Found C, 60.20; H, 13.80; N, 7.85. 1H-NMR(D2O, ppm) 0.98(d, 6H), 1.00(t, 3H), 1.24(s, 6H), 1.63(m, 2H), 2.05(m, 1H), 2.98(t, 2H). MS(m/z) 143(M+). at about 38° C. The mixture was stirred overnight while maintaining the temperature extracted with ether The ether extract washed once with water dried over anhydrous magnesium sulfate After recovering the ether, 6.2 g light yellow liquid was obtained The mixture was refluxed for 10 hours cooled The lower layer of solid was then washed with ether (×3) The resulting washing extract ether dried over anhydrous potassium carbonate filtered To the filtrate, HCl-Et2O was added under cooling until the solution The solid was collected by filtering recrystallized three times from iso-propanol and acetone

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

Procedure: To a solution of 8.25 g (0.15 mole) propionitrile in 25 mL glacial acetic acid, 15 g concentrated sulfuric acid was added dropwise while controlling the reaction temperature at about 38° C., then 5.2 g (0.051 mole) of 2,3-dimethyl-2-butanol was added dropwise at the temperature below 40° C. with stirring. The mixture was stirred overnight while maintaining the temperature, then poured into glacial water, basified with 40% sodium hydroxide solution and extracted with ether. The ether extract was combined, washed once with water, and dried over anhydrous magnesium sulfate. After recovering the ether, 6.2 g light yellow liquid was obtained and solved in 80 mL anhydrous ether. The resulting solution was added dropwise to a suspension of 3.04 g (0.08 mol) lithium aluminium hydride in 80 mL anhydrous ether. The mixture was refluxed for 10 hours, then cooled. To the mixture, proper amount of 40% aqueous sodium hydroxide was added dropwise and the upper layer of ether was carefully poured out. The lower layer of solid was then washed with ether (×3). The resulting washing and extract ether were combined, dried over anhydrous potassium carbonate and filtered. To the filtrate, HCl-Et2O was added under cooling until the solution is acidic. The solid was collected by filtering and recrystallized three times from iso-propanol and acetone to give a white lamellar crystal 3.33 g (yield 46.33%), mp 183-185° C. Elemental analysis for C9H22NCI (%): Calculated C, 10.15; H, 12.34; N, 7.79. Found C, 60.20; H, 13.80; N, 7.85. 1H-NMR(D2O, ppm) 0.98(d, 6H), 1.00(t, 3H), 1.24(s, 6H), 1.63(m, 2H), 2.05(m, 1H), 2.98(t, 2H). MS(m/z) 143(M+). at about 38° C. The mixture was stirred overnight while maintaining the temperature extracted with ether The ether extract washed once with water dried over anhydrous magnesium sulfate After recovering the ether, 6.2 g light yellow liquid was obtained The mixture was refluxed for 10 hours cooled The lower layer of solid was then washed with ether (×3) The resulting washing extract ether dried over anhydrous potassium carbonate filtered To the filtrate, HCl-Et2O was added under cooling until the solution The solid was collected by filtering recrystallized three times from iso-propanol and acetone

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

Procedure: A mixture of 1.0 g of 4-cyano-2-methoxyphenol, 0.6 g of 2,3-dimethyl-2-butanol and 9 ml of acetic acid was slowly added dropwise to 3 ml of concentrated sulfuric acid. The mixture obtained was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was separated with aqueous sodium hydroxide solution and the aqueous layer obtained was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue obtained was subjected to silica gel column chromatography to obtain 0.6 g of N-(1,1,2-trimethylpropyl)-4-hydroxy-3-methoxybenzamide. N-(1,1,2-trimethylpropyl)-4-hydroxy-3-methoxybenzamide: The mixture obtained the mixture was extracted with ethyl acetate The organic layer was separated with aqueous sodium hydroxide solution the aqueous layer obtained extracted with ethyl acetate The organic layer was concentrated under reduced pressure the residue obtained

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

Procedure: A mixture of 1.0 g of 4-cyano-2-methoxyphenol, 0.6 g of 2,3-dimethyl-2-butanol and 9 ml of acetic acid was slowly added dropwise to 3 ml of concentrated sulfuric acid. The mixture obtained was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was separated with aqueous sodium hydroxide solution and the aqueous layer obtained was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue obtained was subjected to silica gel column chromatography to obtain 0.6 g of N-(1,1,2-trimethylpropyl)-4-hydroxy-3-methoxybenzamide. N-(1,1,2-trimethylpropyl)-4-hydroxy-3-methoxybenzamide: The mixture obtained the mixture was extracted with ethyl acetate The organic layer was separated with aqueous sodium hydroxide solution the aqueous layer obtained extracted with ethyl acetate The organic layer was concentrated under reduced pressure the residue obtained