N-(hydroxymethyl)prop-2-enamide

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

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

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately equimolar amounts of N-(2-hydroxyethyl phthalimide (about 5 molar percent excess) and dried IBMA were mixed together in a reaction flask with 0.5 weight percent toluene sulfonic acid, based on the weight of IBMA, and 200 ppm MEHQ added. The nearly dry blend was stirred and heated using an external oil bath. When the temperature reached 65° C., a rapid reaction ensued and the reaction mixture partially liquified. After a short period of time, the reaction rate (as evidenced by the isobutyl alcohol removal) almost stopped, and the reaction mixture solidified. The reaction mixture was then rapidly heated to about 120° C., and the reaction again proceeded vigorously, going to near quantitative yields in a few more minutes. The product was a clear, low viscosity liquid at 120° C. which solidified at about 65° C. to a waxy, opaque white solid which was found to be readily soluble in acrylonitrile. The product was the 2-hydroxyethyl phthalimide ether of N-(hydroxymethyl)acrylamide. added heated reached 65° C. a rapid reaction After a short period of time the reaction rate (as evidenced by the isobutyl alcohol removal) the reaction to near quantitative yields in a few more minutes at 120° C. solidified at about 65° C. to a waxy, opaque white solid which

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately equimolar amounts of N-(2-hydroxyethyl phthalimide (about 5 molar percent excess) and dried IBMA were mixed together in a reaction flask with 0.5 weight percent toluene sulfonic acid, based on the weight of IBMA, and 200 ppm MEHQ added. The nearly dry blend was stirred and heated using an external oil bath. When the temperature reached 65° C., a rapid reaction ensued and the reaction mixture partially liquified. After a short period of time, the reaction rate (as evidenced by the isobutyl alcohol removal) almost stopped, and the reaction mixture solidified. The reaction mixture was then rapidly heated to about 120° C., and the reaction again proceeded vigorously, going to near quantitative yields in a few more minutes. The product was a clear, low viscosity liquid at 120° C. which solidified at about 65° C. to a waxy, opaque white solid which was found to be readily soluble in acrylonitrile. The product was the 2-hydroxyethyl phthalimide ether of N-(hydroxymethyl) acrylamide. added heated reached 65° C. a rapid reaction After a short period of time the reaction rate (as evidenced by the isobutyl alcohol removal) the reaction to near quantitative yields in a few more minutes at 120° C. solidified at about 65° C. to a waxy, opaque white solid which

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately equimolar amounts of N-(2-hydroxyethyl phthalimide (about 5 molar percent excess) and dried IBMA were mixed together in a reaction flask with 0.5 weight percent toluene sulfonic acid, based on the weight of IBMA, and 200 ppm MEHQ added. The nearly dry blend was stirred and heated using an external oil bath. When the temperature reached 65° C., a rapid reaction ensued and the reaction mixture partially liquified. After a short period of time, the reaction rate (as evidenced by the isobutyl alcohol removal) almost stopped, and the reaction mixture solidified. The reaction mixture was then rapidly heated to about 120° C., and the reaction again proceeded vigorously, going to near quantitative yields in a few more minutes. The product was a clear, low viscosity liquid at 120° C. which solidified at about 65° C. to a waxy, opaque white solid which was found to be readily soluble in acrylonitrile. The product was the 2-hydroxyethyl phthalimide ether of N-(hydroxymethyl) acrylamide. added heated reached 65° C. a rapid reaction After a short period of time the reaction rate (as evidenced by the isobutyl alcohol removal) the reaction to near quantitative yields in a few more minutes at 120° C. solidified at about 65° C. to a waxy, opaque white solid which

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

Procedure: A flask was charged with 108 g of o-cresol, 101 g of N-methylolacrylamide, 5 g of 37% aqueous hydrochloric acid solution and 100 ml of acetone, and the mixture was subjected to the condensation reaction at 60° C. for 60 minutes with stirring. The obtained reaction mixture was poured into excess water to separate an organic layer. The organic layer was dissolved in 200 ml of methylene chloride, which was washed with three 100 ml portions of water to give 127 g of N-(3-methyl-4-hydroxybenzyl)acrylamide. the mixture was subjected to the condensation reaction at 60° C. for 60 minutes The obtained reaction mixture to separate an organic layer The organic layer was dissolved in 200 ml of methylene chloride which was washed with three 100 ml portions of water

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

Procedure: A flask was charged with 108 g of o-cresol, 101 g of N-methylolacrylamide, 5 g of 37% aqueous hydrochloric acid solution and 100 ml of acetone, and the mixture was subjected to the condensation reaction at 60° C. for 60 minutes with stirring. The obtained reaction mixture was poured into excess water to separate an organic layer. The organic layer was dissolved in 200 ml of methylene chloride, which was washed with three 100 ml portions of water to give 127 g of N-(3-methyl-4-hydroxybenzyl)acrylamide. the mixture was subjected to the condensation reaction at 60° C. for 60 minutes The obtained reaction mixture to separate an organic layer The organic layer was dissolved in 200 ml of methylene chloride which was washed with three 100 ml portions of water

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

Procedure: A flask equipped with a condenser and a stirrer was charged with 122 g of 2,4-dimethylphenol, 101 g of N-methylolacrylamide, 1.80 g of p-toluenesulfonic acid and 100 ml of acetone, and the mixture was reacted at 60° C. for 60 minutes with stirring. The obtained reaction mixture was poured into excess water to separate an organic layer. The organic layer was dissolved in 200 ml of methylene chloride, which was washed with three 100 ml portions of water to give 174 g of N-(3,5-dimethyl-2-hydroxybenzyl)acrylamide. A flask equipped with a condenser and a stirrer the mixture was reacted at 60° C. for 60 minutes The obtained reaction mixture to separate an organic layer The organic layer was dissolved in 200 ml of methylene chloride which was washed with three 100 ml portions of water

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

Procedure: A flask equipped with a condenser and a stirrer was charged with 122 g of 2,4-dimethylphenol, 101 g of N-methylolacrylamide, 1.80 g of p-toluenesulfonic acid and 100 ml of acetone, and the mixture was reacted at 60° C. for 60 minutes with stirring. The obtained reaction mixture was poured into excess water to separate an organic layer. The organic layer was dissolved in 200 ml of methylene chloride, which was washed with three 100 ml portions of water to give 174 g of N-(3,5-dimethyl-2-hydroxybenzyl)acrylamide. A flask equipped with a condenser and a stirrer the mixture was reacted at 60° C. for 60 minutes The obtained reaction mixture to separate an organic layer The organic layer was dissolved in 200 ml of methylene chloride which was washed with three 100 ml portions of water

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

Procedure: In a 300 cc capacity round bottom flask equipped with a stirrer were put 50.5 g (0.5 mole) of N-methylolacrylamide and 50 cc of water and, as a polymerization-inhibitor, 500 mg of hydroquinone. On the other hand, 43 g (0.5 mole) of morpholine were gradually added thereto while stirring. Afterwards, the entire contents were stirred for 1 hour at 50° to 60°C. The reaction product was concentrated and then recrystallized from ethyl acetate. m.p.; 91°-92°C. In addition, the resulting product was further distilled under reduced pressure to obtain 34.5 g of fraction of 140°-160°C/0.01 mmHg (45.7%). In a 300 cc capacity round bottom flask equipped with a stirrer Afterwards, the entire contents were stirred for 1 hour at 50° to 60°C The reaction product was concentrated recrystallized from ethyl acetate In addition, the resulting product was further distilled under reduced pressure to obtain 34.5 g of fraction of 140°-160°C/0.01 mmHg (45.7%)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately equimolar amounts of N-(2-hydroxyethyl phthalimide (about 5 molar percent excess) and dried IBMA were mixed together in a reaction flask with 0.5 weight percent toluene sulfonic acid, based on the weight of IBMA, and 200 ppm MEHQ added. The nearly dry blend was stirred and heated using an external oil bath. When the temperature reached 65° C., a rapid reaction ensued and the reaction mixture partially liquified. After a short period of time, the reaction rate (as evidenced by the isobutyl alcohol removal) almost stopped, and the reaction mixture solidified. The reaction mixture was then rapidly heated to about 120° C., and the reaction again proceeded vigorously, going to near quantitative yields in a few more minutes. The product was a clear, low viscosity liquid at 120° C. which solidified at about 65° C. to a waxy, opaque white solid which was found to be readily soluble in acrylonitrile. The product was the 2-hydroxyethyl phthalimide ether of N-(hydroxymethyl)acrylamide. added heated reached 65° C. a rapid reaction After a short period of time the reaction rate (as evidenced by the isobutyl alcohol removal) the reaction to near quantitative yields in a few more minutes at 120° C. solidified at about 65° C. to a waxy, opaque white solid which