3-ethenoxypropan-1-amine

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

Procedure: A 500 mL flask was charged with resorcinol (33 g, 300 mmol), 3-amino-1-propanol vinyl ether (61 g, 600 mmol), and paraformaldehyde (38 g, 1260 mmol). Approximately 200 g of toluene was added and the mixture was heated to reflux. Reflux continued until water ceased to collect in the trap (about one hour). The reaction mixture was then cooled to room temperature. A large volume of solid byproduct formed in the reaction vessel. The toluene solution was decanted from the solid, and the remaining solid was washed with extra toluene. All of the toluene fractions were combined in a separatory funnel. The toluene solution was washed with a 5% NaOH solution, followed by a saturated NaCl solution. The toluene solution was dried with magnesium sulfate, and filtered over a small bed of neutral alumina. Removal of the solvent under reduced pressure produced about 50 g of an orange colored liquid (46% yield). the mixture was heated to reflux Reflux to collect in the trap (about one hour) A large volume of solid byproduct formed in the reaction vessel The toluene solution was decanted from the solid the remaining solid was washed with extra toluene All of the toluene fractions were combined in a separatory funnel The toluene solution was washed with a 5% NaOH solution The toluene solution was dried with magnesium sulfate filtered over a small bed of neutral alumina Removal of the solvent under reduced pressure

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

Procedure: This compound was made according to the method outlined in Example 3, by combining phenol (28 g, 300 mmole), 3-amino-1-propanol vinyl ether (30 g, 300 mmole), and paraformaldehyde (19.5 g, (650 mmole) in a 500 ml flask. The water condensate was removed using toluene as the azeotrope solvent. The product was worked-up to obtain 50 g (76% yield) of a light yellow, low viscosity liquid. The water condensate was removed to obtain 50 g (76% yield) of a light yellow, low viscosity liquid

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

Procedure: Hydroquinone (8.23 grams, 75 mmole), 3-amino-1-propanol vinyl ether (15.1 grams, 150 mmole), and toluene (100 mL) were placed in a 250 mL round bottom flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole of formaldehyde) was then added to the flask. The flask was then equipped with a magnetic stir bar, a Dean-Stark trap, and condenser. The mixture was stirred and heated to reflux under an argon blanket. A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux. The reaction mixture had turned black by this point. The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide, followed by one 50 mL aliquot of water. The toluene solution was passed over a bed of neutral alumina and then evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid. The flask was then equipped with a magnetic stir bar heated to reflux under an argon blanket A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid

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

Procedure: A 500 mL flask was charged with resorcinol (33 g, 300 mmol), 3-amino-1-propanol vinyl ether (61 g, 600 mmol), and paraformaldehyde (38 g, 1260 mmol). Approximately 200 g of toluene was added and the mixture was heated to reflux. Reflux continued until water ceased to collect in the trap (about one hour). The reaction mixture was then cooled to room temperature. A large volume of solid byproduct formed in the reaction vessel. The toluene solution was decanted from the solid, and the remaining solid was washed with extra toluene. All of the toluene fractions were combined in a separatory funnel. The toluene solution was washed with a 5% NaOH solution, followed by a saturated NaCl solution. The toluene solution was dried with magnesium sulfate, and filtered over a small bed of neutral alumina. Removal of the solvent under reduced pressure produced about 50 g of an orange colored liquid (46% yield). the mixture was heated to reflux Reflux to collect in the trap (about one hour) A large volume of solid byproduct formed in the reaction vessel The toluene solution was decanted from the solid the remaining solid was washed with extra toluene All of the toluene fractions were combined in a separatory funnel The toluene solution was washed with a 5% NaOH solution The toluene solution was dried with magnesium sulfate filtered over a small bed of neutral alumina Removal of the solvent under reduced pressure

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

Procedure: This compound was made according to the method outlined in Example 3, by combining phenol (28 g, 300 mmole), 3-amino-1-propanol vinyl ether (30 g, 300 mmole), and paraformaldehyde (19.5 g, (650 mmole) in a 500 ml flask. The water condensate was removed using toluene as the azeotrope solvent. The product was worked-up to obtain 50 g (76% yield) of a light yellow, low viscosity liquid. The water condensate was removed to obtain 50 g (76% yield) of a light yellow, low viscosity liquid

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

Procedure: Hydroquinone (8.23 grams, 75 mmole), 3-amino-1-propanol vinyl ether (15.1 grams, 150 mmole), and toluene (100 mL) were placed in a 250 mL round bottom flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole of formaldehyde) was then added to the flask. The flask was then equipped with a magnetic stir bar, a Dean-Stark trap, and condenser. The mixture was stirred and heated to reflux under an argon blanket. A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux. The reaction mixture had turned black by this point. The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide, followed by one 50 mL aliquot of water. The toluene solution was passed over a bed of neutral alumina and then evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid. The flask was then equipped with a magnetic stir bar heated to reflux under an argon blanket A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid

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

Procedure: Hydroquinone (8.23 grams, 75 mmole), 3-amino-1-propanol vinyl ether (15.1 grams, 150 mmole), and toluene (100 mL) were placed in a 250 mL round bottom flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole of formaldehyde) was then added to the flask. The flask was then equipped with a magnetic stir bar, a Dean-Stark trap, and condenser. The mixture was stirred and heated to reflux under an argon blanket. A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux. The reaction mixture had turned black by this point. The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide, followed by one 50 mL aliquot of water. The toluene solution was passed over a bed of neutral alumina and then evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid. The flask was then equipped with a magnetic stir bar heated to reflux under an argon blanket A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid

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

Procedure: A 500 mL flask was charged with resorcinol (33 g, 300 mmol), 3-amino-1-propanol vinyl ether (61 g, 600 mmol), and paraformaldehyde (38 g, 1260 mmol). Approximately 200 g of toluene was added and the mixture was heated to reflux. Reflux continued until water ceased to collect in the trap (about one hour). The reaction mixture was then cooled to room temperature. A large volume of solid byproduct formed in the reaction vessel. The toluene solution was decanted from the solid, and the remaining solid was washed with extra toluene. All of the toluene fractions were combined in a separatory funnel. The toluene solution was washed with a 5% NaOH solution, followed by a saturated NaCl solution. The toluene solution was dried with magnesium sulfate, and filtered over a small bed of neutral alumina. Removal of the solvent under reduced pressure produced about 50 g of an orange colored liquid (46% yield). the mixture was heated to reflux Reflux to collect in the trap (about one hour) A large volume of solid byproduct formed in the reaction vessel The toluene solution was decanted from the solid the remaining solid was washed with extra toluene All of the toluene fractions were combined in a separatory funnel The toluene solution was washed with a 5% NaOH solution The toluene solution was dried with magnesium sulfate filtered over a small bed of neutral alumina Removal of the solvent under reduced pressure

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

Procedure: This compound was made according to the method outlined in Example 3, by combining phenol (28 g, 300 mmole), 3-amino-1-propanol vinyl ether (30 g, 300 mmole), and paraformaldehyde (19.5 g, (650 mmole) in a 500 ml flask. The water condensate was removed using toluene as the azeotrope solvent. The product was worked-up to obtain 50 g (76% yield) of a light yellow, low viscosity liquid. The water condensate was removed to obtain 50 g (76% yield) of a light yellow, low viscosity liquid

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

Procedure: Hydroquinone (8.23 grams, 75 mmole), 3-amino-1-propanol vinyl ether (15.1 grams, 150 mmole), and toluene (100 mL) were placed in a 250 mL round bottom flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole of formaldehyde) was then added to the flask. The flask was then equipped with a magnetic stir bar, a Dean-Stark trap, and condenser. The mixture was stirred and heated to reflux under an argon blanket. A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux. The reaction mixture had turned black by this point. The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide, followed by one 50 mL aliquot of water. The toluene solution was passed over a bed of neutral alumina and then evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid. The flask was then equipped with a magnetic stir bar heated to reflux under an argon blanket A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid

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

Procedure: A 500 mL flask was charged with resorcinol (33 g, 300 mmol), 3-amino-1-propanol vinyl ether (61 g, 600 mmol), and paraformaldehyde (38 g, 1260 mmol). Approximately 200 g of toluene was added and the mixture was heated to reflux. Reflux continued until water ceased to collect in the trap (about one hour). The reaction mixture was then cooled to room temperature. A large volume of solid byproduct formed in the reaction vessel. The toluene solution was decanted from the solid, and the remaining solid was washed with extra toluene. All of the toluene fractions were combined in a separatory funnel. The toluene solution was washed with a 5% NaOH solution, followed by a saturated NaCl solution. The toluene solution was dried with magnesium sulfate, and filtered over a small bed of neutral alumina. Removal of the solvent under reduced pressure produced about 50 g of an orange colored liquid (46% yield). the mixture was heated to reflux Reflux to collect in the trap (about one hour) A large volume of solid byproduct formed in the reaction vessel The toluene solution was decanted from the solid the remaining solid was washed with extra toluene All of the toluene fractions were combined in a separatory funnel The toluene solution was washed with a 5% NaOH solution The toluene solution was dried with magnesium sulfate filtered over a small bed of neutral alumina Removal of the solvent under reduced pressure

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

Procedure: This compound was made according to the method outlined in Example 3, by combining phenol (28 g, 300 mmole), 3-amino-1-propanol vinyl ether (30 g, 300 mmole), and paraformaldehyde (19.5 g, (650 mmole) in a 500 ml flask. The water condensate was removed using toluene as the azeotrope solvent. The product was worked-up to obtain 50 g (76% yield) of a light yellow, low viscosity liquid. The water condensate was removed to obtain 50 g (76% yield) of a light yellow, low viscosity liquid