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Acetic Anhydride → 2-Propenoic acid, 2-(acetyloxy)-, ethyl ester

HRID 868771
Notes
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Reaction equation

HRID 868771 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].[C:9](OC(=O)C)(=[O:11])[CH3:10]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C>[C:9]([O:3][C:2](=[CH2:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])(=[O:11])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 12041Ethyl pyruvate

Product 1

HCID 112173872-Propenoic acid, 2-(acetyloxy)-, ethyl esterYield 58.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °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%).

Workup

  1. additionwas added
  2. customto obtain a reaction solution
  3. customwas removed from the reaction solution
  4. distillationThereafter, the residue was purified by reduced pressure distillation (35 to 40 mmHg, 90 to 103° C.)

Sources & evidence

ORD record
ord-8145e7bb54f94012b03842a0a38f85ab
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08968975B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes