Réaction #955953

ord-8145e7bb54f94012b03842a0a38f85ab

Équation de réaction

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
Rendement 58.5%

Solvants

Conditions de réaction

Température
120°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added
  2. 2
    Autreto obtain a reaction solution
  3. 3
    Autrewas 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.)

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08968975B2uspto-grants-2015_03