Ethanol → 4-(3-Chlorophenyl)-4-oxobutanoic acid

HRID 1493

Reaction equation

HRID 1493 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=O.C(OC)(=O)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20]>CCOCC>[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 7820Dimethyl Succinate2×HCID 17946Methyl 3-chlorobenzoateHCID 5360545Sodium

Product 1

HCID 27578284-(3-Chlorophenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evaporator to yield a greenish paste which was slurried in 100 ml ether and an additional 2 ml of dimethyl succinate was added. The reaction was evaporated to a paste, quenched with water and extracted with ether. The ether extracts were washed with water and brine, dried and evaporated in vacuo.

Workup

  1. stirringthe mixture was stirred for 5 minutes at room temperature
  2. concentrationThe mixture was slowly concentrated on a rotary evaporator
  3. customto yield a greenish paste which
  4. customThe reaction was evaporated to a paste
  5. customquenched with water
  6. extractionextracted with ether
  7. washThe ether extracts were washed with water and brine
  8. customdried
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ce064075330c45f48a8cd178fcf95efd
Source dataset
uspto-grants-1998_03
Patent number
US05726162

Linked notes

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