Methyl α-methoxy-γ-oxobenzenebutanoate → Methyl-4-oxo-4-phenyl-2-butenoate

HRID 982181Notes

Reaction equation

HRID 982181 reaction equation
[C:1]([CH2:9][CH:10](OC)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[C:1](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 13934019Methyl α-methoxy-γ-oxobenzenebutanoate

Product 1

HCID 1484788Methyl-4-oxo-4-phenyl-2-butenoateYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 268 mg of methyl β-benzoyl-α-methoxypropionate, 150 mg of paratoluenesulfonic acid monohydrate and 5 ml of toluene was stirred at 80° C. for 1 hour. A pressure was reduced with an aspirator and a total amount of the resultant was reduced to 1/2 by concentration. The resultant was stirred at 80° C. for 20 minutes and was left for cooling. The reaction mixture was distributed between ethyl acetate and water and the ethyl acetate layer was washed with a saturated solution of NaHCO3 and then with water, and was dried with anhydrous magnesium sulfate. The solvent was distilled away to give 206 mg of methyl trans-β-benzoylacrylate as a yellow oil.

Workup

  1. concentrationa total amount of the resultant was reduced to 1/2 by concentration
  2. stirringThe resultant was stirred at 80° C. for 20 minutes
  3. waitwas left
  4. temperaturefor cooling
  5. washthe ethyl acetate layer was washed with a saturated solution of NaHCO3
  6. dry with materialwith water, and was dried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-90951170d11443ccbee000e8a444a528
Source dataset
uspto-grants-1991_02
Patent number
US04994600

Reaction notes

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