Ethanol → 3-Fluoro-6-(phenylthio)-phenylacetic acid

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](CC#N)[C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[CH2:18]([OH:20])[CH3:19].[OH-:21].[K+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH2:19][C:18]([OH:21])=[O:20])[C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

Procedure

80 g of 3-fluoro-6-(phenylthio)-phenylacetonitrile, 225 ml of ethanol, 75.5 g of potassium hydroxide and 225 ml of water are heated under reflux for 9 hours. The ethanol is subsequently evaporated off under reflux and the residue treated with water until completely dissolved, whereafter the neutral constituents are extracted with benzene. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with chloroform. The organic phase is washed with water, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 3-fluoro-6-(phenylthio)-phenylacetic acid which melts at 80°-83° C.