Ethanol → 2-Phenylthio-5-trifluoromethylbenzoic acid
Reaction equation
[C:1]1([S:7][C:8]2C=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2C#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>O>[C:1]1([S:7][C:8]2[CH:9]=[CH:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:23]=2[C:22]([OH:20])=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
6 g of 2-(phenylthio)-5-trifluoromethyl-benzonitrile, 40 ml of 15% aqueous sodium hydroxide solution and 12 ml of ethanol are heated under reflux for 12 hours and then cooled. After the addition of 100 ml of water, the mixture is extracted with 80 ml of benzene. The aqueous phase is cooled to 0° C and acidified with concentrated hydrochloric acid. The precipitate which separates out is extracted with methylene chloride. The organic phase is washed with water until neutral, dried over sodium sulphate, filtered and evaporated. There is obtained 2-(phenylthio)-5-trifluoromethyl-benzoic acid which melts at 140°-145° C.
Workup
- temperatureunder reflux for 12 hours
- temperaturecooled
- extractionthe mixture is extracted with 80 ml of benzene
- extractionThe precipitate which separates out is extracted with methylene chloride
- washThe organic phase is washed with water until neutral,
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-808760e5b6ba4c0c9333276f1be42940
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04006145
Reaction notes
Loading…