Sulfuric Acid → Ethyl 3-(4-chlorophenyl)-3-oxopropanoate

HRID 1599979Notes

Reaction equation

HRID 1599979 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].CC([O-])(C)C.[K+].[C:17](=O)([O:21]CC)[O:18][CH2:19][CH3:20].S(=O)(=O)(O)O>>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([CH2:1][C:17]([O:18][CH2:19][CH3:20])=[O:21])=[O:3])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7467P-ChloroacetophenoneHCID 7766Diethyl CarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoate

Procedure

200 g (1.29 mol) of 4-chloroacetophenone (dissolved in 500 ml of diethyl carbonate) were added dropwise at 60° C. to a mixture of 296.4 g (2.59 mol) of potassium tert-butylate and 2.25 1 of diethyl carbonate. Thesuspension, which could be stirred with difficulty, was stirred at 60° C. for 3 h and then introduced into 2.7 1 of 10% strength sulfuric acid. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate and concentration in vacuo gave the crude product, which was purified further by distillation (b.p. 130° C., 0.4 mbar). Yield: 268 g.

Workup

  1. stirringwas stirred at 60° C. for 3 h
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying of the organic phase over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-3899ab47bee944ab98cc0f441c85152b
Source dataset
uspto-grants-1998_04
Patent number
US05744426

Reaction notes

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