Reaction #955955

ord-c044d2a1fa244dfd88caa39a2fce939c

Reaction equation

CC(=O)OC(C)=O
acetic anhydride
CCCCOC(=O)C(C)=O
butyl pyruvate
CC(=O)OC(C)=O
acetic anhydride
C=C(OC(C)=O)C(=O)OCCCC
butyl α-acetoxyacrylate
Yield 67.1%

Solvents

Conditions

Temperature
120°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    Otherto obtain a second reaction solution
  3. 3
    Otherwas removed from the second reaction solution
  4. 4
    workup.DISTILLATIONThereafter, the residue was purified by reduced pressure distillation (2 mmHg, 56 to 63° C.)

Procedure

Next, in a mixture of the obtained butyl pyruvate (235 g, 1.6 mol) and acetic anhydride (333 g, 3.3 mol), p-toluenesulfonic acid monohydrate (5 g) was added. Then, the mixture was stirred under a nitrogen gas stream at 120° C. for 25 hours to obtain a second reaction solution. Next, acetic acid generated by a reaction with excess acetic anhydride under reduced pressure (5 mmHg) was removed from the second reaction solution. Thereafter, the residue was purified by reduced pressure distillation (2 mmHg, 56 to 63° C.) to obtain butyl α-acetoxyacrylate (200 g, yield 67%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08968975B2uspto-grants-2015_03