1-Indanone → 2-(p-Chlorobenzylidene)-1-indanone

Reaction equation

[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[OH-].[K+]>C(O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:14][CH:13]=1

Participants

Procedure

A mixture of 100 g of indanone, 112 g of p-chlorobenzaldehyde and 500 ml of ethanol is stirred, the resulting solution is cooled to -10° and treated rapidly (3 minutes) with a solution of 5.0 g of KOH in 100 ml of ethanol. The solution is allowed to warm and the product begins to crystallize at 17° (cooled to keep under 15°). The resulting slurry is allowed to stir at 20°-25° for 1 hour, and then poured onto 2 liters of icewater. After standing for 3 hours, the solid is filtered, washed with cold water and allowed to air dry; wt., 190 g, m.p. 174°-179°. After crystallization from 400 ml of DMF, the cream-colored solid weighs 164.5 g (86%), m.p. 177°-179°.