P-Chloroacetophenone → HCID 3456926, compound

HRID 1382485Notes

Reaction equation

HRID 1382485 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].C[O-].[Na+].[CH:14](OCC)=[O:15]>C(OCC)C>[OH:15][CH:14]=[CH:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 8025Ethyl formateHCID 10942334Sodium Methoxide

Product 1

HCID 3456926HCID 3456926, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

300 g (1.94 moles) of 4-chloroacetophenone are added dropwise to a suspension of 105 g (1.94 moles) of sodium methylate in 1.7 l of diethyl ether. 144 g (1.94 moles) of ethyl formate are added dropwise at room temperature, with cooling. The reaction mixture is stirred under reflux for 3 hours and cooled to room temperature and the precipitate is filtered off with suction. The precipitate is dissolved in water, the pH value is brought to 1-2 with dilute hydrochloric acid, the mixture is extracted with ethyl acetate and the organic phase is concentrated. 216 g (61% of theory) of 4-chlorophenyl hydroxyvinyl ketone of melting point 44° C. are obtained.

Workup

  1. temperaturewith cooling
  2. temperatureunder reflux for 3 hours
  3. filtrationthe precipitate is filtered off with suction
  4. dissolutionThe precipitate is dissolved in water
  5. extractionthe mixture is extracted with ethyl acetate
  6. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-46502e12513643be97abba8714a46f76
Source dataset
uspto-grants-1989_02
Patent number
US04806644

Reaction notes

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