Ethanol → Ethyl 4-(2-methylphenyl)-3-oxobutanoate

HRID 26228Notes

Reaction equation

HRID 26228 reaction equation
C([CH:4]([C:10](=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)C.C(O)C.[O-]CC.[Na+]>O>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:10](=[O:19])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 21325237Ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate

Product 1

HCID 21325235Ethyl 4-(2-methylphenyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the method of Hunsdiecker [Berichte, 75, 454 (1942)], 26 parts of ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate was stirred for 10 hours at room temperature with 100 parts ethanol and 6.8 parts of sodium ethoxide. The mixture was diluted with water and extracted with ether. The solvent was then evaporated to give ethyl 4-(2-methylphenyl)-3-oxobutanoate.

Workup

  1. extractionextracted with ether
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-9a083714fcfe4da197ac1521891f6029
Source dataset
uspto-grants-1979_04
Patent number
US04148918

Reaction notes

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