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

HRID 1741223Notes

Reaction equation

HRID 1741223 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[O:3].[C:8](OC(=O)C)(=[O:10])[CH3:9]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>[C:8]([O:3][C:2](=[CH2:4])[C:1]([O:6][CH3:7])=[O:5])(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11748Methyl pyruvate

Product 1

HCID 111372772-Propenoic acid, 2-(acetyloxy)-, methyl esterYield 34.7%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 962WaterSolvent

Procedure

102.1 Grams(1 mole) of methyl pyruvate is dissolved in 204.2 g(2 moles) of acetic anhydride and 5.0 g(20 millimoles) of pyridinium p-toluenesulfonate is added thereto, followed by conducting a reaction at 100 to 110° C. for 7 hours with stirring and refluxing with stirring for 11 hours. After cooling, the reaction solution is poured into 5000 ml of water and the precipitated oily substance is extracted with ethyl ether. The extract layer is washed with water, dried over anhydrous magnesium sulfate, concentrated and distilled under reduced pressure to give 50.0 g of methyl 2-acetyloxyacrylate as colorless oil having bp. 65 to 68° C./11 mmHg.

Workup

  1. customa reaction at 100 to 110° C. for 7 hours
  2. temperaturerefluxing
  3. stirringwith stirring for 11 hours
  4. temperatureAfter cooling
  5. extractionthe precipitated oily substance is extracted with ethyl ether
  6. washThe extract layer is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-b98fc868e3464f098f4dda1eeca1bce7
Source dataset
uspto-grants-1999_10
Patent number
US05973094

Reaction notes

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