4'-Methoxyacetophenone → Ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxobutanoate

HRID 1990772Notes

Reaction equation

HRID 1990772 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[O:14]>C1(C)C=CC=CC=1>[OH:14][CH:13]([CH2:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:11])[C:12]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 74764'-MethoxyacetophenoneHCID 70211Ethyl oxoacetate

Product 1

HCID 23153694Ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxobutanoateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15.02 g (0.10 mol) of 4′-methoxyacetophenone and a 45% toluene solution (25 ml) of ethyl glyoxalate were stirred overnight at 100° C. The reaction liquid was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 20.62 g (yield: 82%) of ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxo-butyrate as a yellow oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-1670e1e595e1458ba0706650aa633322
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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