P-Chloroacetophenone → Ethyl 3-(4-chlorophenyl)-3-oxopropanoate

HRID 436901Notes

Reaction equation

HRID 436901 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].[H-].[Na+].[C:13](=O)([O:17]CC)[O:14][CH2:15][CH3:16]>>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:13]([O:14][CH2:15][CH3:16])=[O:17])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

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

Procedure

The starting material is prepared as follows: A solution of 96.6 g of 4-chloro acetophenone in 300 ml of diethyl carbonate is added dropwise to a suspension of 34 g sodium hydride (55% in mineral oil, washed twice with diethyl ether) in 400 ml of diethyl carbonate at ice bath temperature, then at room temperature for 2 days. To the dark solution is then added crushed ice and 5N hydrochloric acid to adjust the pH to 6-7. After dilution with diethyl ether, the layers are separated, the organic phase washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. After removal of the solvents, the oily ethyl 3-(4-chloro-phenyl)-3-oxo-propionate is obtained.

Workup

  1. customThe starting material is prepared
  2. washwashed twice with diethyl ether) in 400 ml of diethyl carbonate at ice bath temperature
  3. additionTo the dark solution is then added
  4. customcrushed ice and 5N hydrochloric acid
  5. customAfter dilution with diethyl ether, the layers are separated
  6. washthe organic phase washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removal of the solvents

Sources & evidence

ORD record
ord-59fd556cd5d4406f8786802ef4bbe8d5
Source dataset
uspto-grants-1977_06
Patent number
US04028381

Reaction notes

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