Acetic Anhydride → (Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate

HRID 1701582Notes

Reaction equation

HRID 1701582 reaction equation
[C:1]1([CH2:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:15]([O:14]/[C:8](=[CH:7]\[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)/[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 7918Acetic Anhydride2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 12292599Ethyl 2-oxo-3-phenylpropanoate

Product 1

HCID 11096520(Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate

Procedure

A solution containing 22 g. of ethyl phenylpyruvate, 65 g. of acetic anhydride and 20 mg. of p-toluenesulfonic acid monohydrate was refluxed for 2.5 hours. Excess acetic anhydride was stripped from the reaction mass and the product, crude (Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate, was distilled at about 1.6 mm. Hg. (b.p. 120°-135° C.). The recovered product crystallized on standing in refrigeration and was recovered by filtration and recrystallized from ethanol; recovered 12.1 g., m.p. 41°-47° C.; second recrystallization, 10.5 g., m.p. 47°-49° C.; third recrystallization, 9.2 g., m.p., 47°-49° C.

Workup

  1. additionA solution containing 22 g
  2. distillationthe product, crude (Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate, was distilled at about 1.6 mm. Hg
  3. customThe recovered product crystallized
  4. filtrationwas recovered by filtration
  5. customrecrystallized from ethanol
  6. customrecovered 12.1 g
  7. customsecond recrystallization, 10.5 g
  8. customthird recrystallization, 9.2 g
  9. customm.p., 47°-49° C.

Sources & evidence

ORD record
ord-0be30e25d0c740dca614e379a8f374f5
Source dataset
uspto-grants-1980_03
Patent number
US04194051

Reaction notes

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