Acetic Anhydride → HCID 14984434, compound

HRID 868773

Reaction equation

HRID 868773 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:5])[C:2]([CH3:4])=[O:3].[C:11](OC(=O)C)(=[O:13])[CH3:12]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C>[C:11]([O:3][C:2](=[CH2:4])[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:5])(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 523883Butyl pyruvate

Product 1

HCID 14984434HCID 14984434, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °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%).

Workup

  1. additionwas added
  2. customto obtain a second reaction solution
  3. customwas removed from the second reaction solution
  4. distillationThereafter, the residue was purified by reduced pressure distillation (2 mmHg, 56 to 63° C.)

Sources & evidence

ORD record
ord-c044d2a1fa244dfd88caa39a2fce939c
Source dataset
uspto-grants-2015_03
Patent number
US08968975B2

Linked notes

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