P-Chloroacetophenone → 4-(4-Chlorophenyl)-2-hydroxy-4-oxobutanoic acid

HRID 1818657Notes

Reaction equation

HRID 1818657 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9]>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH2:7][CH:3]([OH:4])[C:2]([OH:6])=[O:5])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 30672534-(4-Chlorophenyl)-2-hydroxy-4-oxobutanoic acid

Procedure

A mixture of glyoxylic acid monohydrate (4.6 g, 50 mmol) and 4-chloroacetophenone (15.4 g, 0.1 mol) are heated at +95° C. under reduced pressure (50 mbar) for 3 hours. During this time, water is continually removed. After cooling, the reaction mixture is taken up in aqueous sodium carbonate solution and extracted with diethyl ether. The aqueous layer is acidified with 15% hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and evaporated, the residue is crystallized from ethyl acetate/hexane to obtain 4-(4-chloro-phenyl)-2-hydroxy-4-oxo-butyric acid.

Workup

  1. temperatureare heated at +95° C. under reduced pressure (50 mbar) for 3 hours
  2. customDuring this time, water is continually removed
  3. temperatureAfter cooling
  4. extractionextracted with diethyl ether
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. customevaporated
  8. customthe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cf689fb383fb493286529b69ad3afe40
Source dataset
uspto-grants-2009_10
Patent number
US07601674B2

Reaction notes

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