Potassium Hydroxide → (6-Chloro-2-ethyl-2-methyl-2,3-dihydro-1H-inden-5-yl)acetic acid

Reaction equation

[OH-].[K+].C[O:4][C:5](=[O:20])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[CH2:12][C:11]([CH2:18][CH3:19])([CH3:17])[CH2:10]2>O.CO>[CH2:18]([C:11]1([CH3:17])[CH2:10][C:9]2[C:13](=[CH:14][C:15]([Cl:16])=[C:7]([CH2:6][C:5]([OH:20])=[O:4])[CH:8]=2)[CH2:12]1)[CH3:19]

Participants

Procedure

A solution of 20 g of potassium hydroxide in 40 cc of water is added to a solution of 11.5 g of 2-ethyl-6-chloro-2-methyl-5-indanacetic acid methyl ester in 250 cc of methanol, and the solution is boiled at reflux for one hour. The cooled solution is concentrated, diluted with water and the neutral components are extracted with ether. The aqueous phase is acidified with hydrochloric acid, extracted with ether, the ether extract is washed with water, dried over sodium sulphate and concentrated by evaporation. The resulting 2-ethyl-6-chloro-2-methyl-5-indanacetic acid is recrystallized from hexane and has a M.P. of 87°-89°.