Water → HCID 21495680, compound
Reaction equation
O.[OH-].[K+].[C:4]([C:12]1[CH:13]=[C:14]([CH2:18][CH:19]([OH:26])[CH2:20][C:21]([O:23]CC)=[O:22])[CH:15]=[CH:16][CH:17]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[C:4]([C:12]1[CH:13]=[C:14]([CH2:18][CH:19]([OH:26])[CH2:20][C:21]([OH:23])=[O:22])[CH:15]=[CH:16][CH:17]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
2.7 ml of water and 1.4 ml of 12.5N potassium hydroxide were added to a solution of 2.7 g of ethyl 4-(m-benzoylphenyl)-3-hydroxy-butyrate in 27ml of ethanol and the mixture was refluxed for 11/2 hours and then evaporated to dryness. The residue was taken up in 27 ml of water and the solution was treated with activated carbon, filtered and acidified to a pH of 1 by adding 10 ml of 2N hydrochloric acid with stirring at 10°C. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness to obtain 2.36 g of 4-(m-benzoyl-phenyl)-3-hydroxy-butyric acid in the form of a colorless amorphous solid soluble in chloroform and insoluble in water.
Workup
- temperaturethe mixture was refluxed for 11/2 hours
- customevaporated to dryness
- additionthe solution was treated with activated carbon
- filtrationfiltered
- additionby adding 10 ml of 2N hydrochloric acid
- extractionThe mixture was extracted with methylene chloride
- washthe organic phase was washed with water
- dry with materialdried over sodium sulfate
- additiontreated with activated carbon
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-a61b236bd60b40c6976090e6baac86f0
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931302
Reaction notes
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