Ethanol → HCID 21495614, compound

HRID 1579779Notes

Reaction equation

HRID 1579779 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:24])[CH:16]([OH:23])[CH2:17][C:18]([O:20]CC)=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>O>[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:24])[CH:16]([OH:23])[CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 21495604HCID 21495604, compound

Product 1

HCID 21495614HCID 21495614, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 818 mg of ethyl 4-(m-benzoyl-phenyl)-3-hydroxy-4-methyl-butyrate, 8 ml of ethanol, 0.8 ml of water and 0.2 ml of 14N potassium hydroxide was refluxed for 11/2 hours and then was evaporated to dryness under reduced pressure. The residue was taken up in 20 ml of water and the solution was acidified to a pH of 1 by progressive addition of a 1N hydrochloric acid solution and was then extracted with methylene chloride. The organic phase was washed with water and evaporated to dryness under reduced pressure to obtain 4-(m-benzoyl-phenyl)-3-hydroxy-4-methyl-butyric acid in the form of a product soluble in alcohols, methylene chloride and chloroform.

Workup

  1. temperaturewas refluxed for 11/2 hours
  2. customwas evaporated to dryness under reduced pressure
  3. additionthe solution was acidified to a pH of 1 by progressive addition of a 1N hydrochloric acid solution
  4. extractionwas then extracted with methylene chloride
  5. washThe organic phase was washed with water
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-27df76a8e99149bd9ebbfc0791c39a62
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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