Hydrochloric Acid → HCID 178468152, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of chlorobenzene (1500 g, 13.3 moles) and aluminum chloride (1080 g, 8.1 moles), a mixture of acetyl chloride (473 g, 6.0 moles) and cyclohexene (555 g, 6.8 moles) was dropwise added in about 3 hours while maintaining the temperature at a level of not higher than -20° C. After the dropwise addition, the reaction system was brought to room temperature. After the termination of the generation of hydrogen chloride gas, the reaction mixture was poured into 5 l of 1:1 hydrochloric acid. After separating the organic layer, the aqueous layer was extracted with diethyl ether, and the organic layers thereby obtained were put together and then dried. The solvent was distilled off by an evaporator. The remaining oily substance was distilled under reduced pressure, whereby 1131 g of a fraction having a boiling point of from 120° to 130° C./0.1 mmHg was obtained. To this fraction, 2 l of a 1:1 mixture of methanol and ethanol was added, and the mixture was cooled in a dry ice/methanol bath to obtain crude crystals. The crude crystals were recrystallized from 500 ml of methanol, whereby 165 g of trans-4-(p-chlorophenyl)-1-acetyl-cyclohexane was obtained. The yield was 12%, and the melting point was 74.6° C.

Provenance & Evidence