P-Chloroacetophenone → 1-(4-Chlorophenyl)butane-1,3-dione

HRID 2285963Notes

Reaction equation

HRID 2285963 reaction equation
C(OC(=O)C[CH:6]([C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:7]([CH3:9])=[O:8])C.ClC1C=CC(C(=O)C)=CC=1.[H-].[Na+]>C(OC(=O)C)C>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([CH2:6][C:7](=[O:8])[CH3:9])=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 24758Sodium hydrideHCID 544551833-(p-Chlorobenzoyl)-levulinic acid ethyl ester

Product 1

HCID 2380831-(4-Chlorophenyl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 3-(p-chlorobenzoyl)-levulinic acid ethyl ester used in Example 20 as the starting material was obtained in the following manner: p-chloro-acetophenone, acetic acid ethyl ester and sodium hydride were condensed to form p-chloro-benzoylacetone by the method described by Swamer and Hauser, J. Am. Chem. So. 72, 1352 (1952). The p-chlorobenzoylacetone thus obtained was alkylated by reaction with bromoacetic acid ester and sodium hydride in dimethyl formamide to produce 3-(p-chlorobenzoyl)-levulinic acid ethyl ester in a yield of 83%, having a boiling point Kp0.001 of 140°-150° C.

Workup

  1. customwas obtained in the following manner
  2. customcondensed

Sources & evidence

ORD record
ord-617e1bf3adf749f59112ffcf5698cae5
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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