Hydrochloric Acid → 5-(2-chloroethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Participants

Reaction Steps

In the same manner as in (2) in Example 2, hydrogen chloride gas was bubbled into the mixture of 20.6 g (0.1 mol) of 10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene (4c), 41 g of acetic acid, and 4.5 g (0.15 mol) of paraformaldehyde. After reaction was conducted, the reaction product was extracted with toluene, neutralized with a saturated sodium bicarbonate solution, and washed with water. Further, this product was dried with sodium sulfate anhydride, concentrated and then recrystallized from hexane to obtain 23.4 g of the compound (5c). Theoretical yield, 92.0%; m.p., 103°-104° C.

Provenance & Evidence