Hydrochloric Acid → HCID 22420402, compound

Participants

Reaction Conditions

Reaction Steps

First, 4-cyanobenzoyl chloride (25 g, 0.15 mole) is added dropwise over 15 minutes with vigorous stirring to aluminum chloride (24.2 g, 0.18 mole) in heptylbenzene (300 ml). The mixture is heated (90° C. for 30 minutes) and then mixed with ice (1 kg) and concentrated hydrochloric acid (100 ml). The resulting suspension is extracted with ether (5×100 ml). The extract is washed with 2N sodium hydroxide (2×100 ml), dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is triturated with hexane (3×100 ml). The hexane solutions are combined, filtered, concentrated and chromatographed on silica gel to give 4'-n-heptyl-4-cyano-benzophenone (14.4 g). This product is heated under reflux in a mixture of 75% sulfuric acid (100 ml) and acetic acid (75 ml) for 30 minutes. The reaction mixture is cooled, diluted with water (200 ml) and filtered. The insoluble solid is recrystallized from aqueous ethanol to give 4-(4-n-heptylbenzoyl)benzoic acid (12.7 g) as cream colored crystals, m.p. 181° C.

Provenance & Evidence