Reaction #955953

Reaction equation

acetic anhydride

ethyl pyruvate

acetic anhydride

→

ethyl α-acetoxyacrylate

Yield 58.5%

Solvents

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherto obtain a reaction solution
3. 3
   Otherwas removed from the reaction solution
4. 4
   workup.DISTILLATIONThereafter, the residue was purified by reduced pressure distillation (35 to 40 mmHg, 90 to 103° C.)

Procedure

First, to a mixture of ethyl pyruvate (315 g, 2.7 mol) and acetic anhydride (554 g, 5.4 mol), p-toluenesulfonic acid monohydrate (8 g) was added. Then, the mixture was stirred under a nitrogen gas stream at 120° C. for 24 hours to obtain a reaction solution. Next, acetic acid generated by a reaction with excess acetic anhydride under reduced pressure (40 to 50 mmHg) was removed from the reaction solution. Thereafter, the residue was purified by reduced pressure distillation (35 to 40 mmHg, 90 to 103° C.) to obtain ethyl α-acetoxyacrylate (250 g, yield 58%).

Source