Ethanol → 2-Phenylthio-5-trifluoromethylbenzoic acid

HRID 435715Notes

Reaction equation

HRID 435715 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]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14895212-(Phenylthio)-5-(trifluoromethyl)benzonitrile

Product 1

HCID 1042312-Phenylthio-5-trifluoromethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperatureunder reflux for 12 hours
  2. temperaturecooled
  3. extractionthe mixture is extracted with 80 ml of benzene
  4. extractionThe precipitate which separates out is extracted with methylene chloride
  5. washThe organic phase is washed with water until neutral,
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e8563dec03664a4b842a7d5bb98c510b
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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