Reacción #955953

ord-8145e7bb54f94012b03842a0a38f85ab

Ecuación de reacción

CC(=O)OC(C)=O
acetic anhydride
CCOC(=O)C(C)=O
ethyl pyruvate
CC(=O)OC(C)=O
acetic anhydride
C=C(OC(C)=O)C(=O)OCC
ethyl α-acetoxyacrylate
Rendimiento 58.5%

Disolventes

Condiciones de reacción

Temperatura
120°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    Otroto obtain a reaction solution
  3. 3
    Otrowas 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.)

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08968975B2uspto-grants-2015_03