p-Toluenesulfonic acid → 6,7-dihydro-5H-benzo(7)annulene

Participants

Reaction Steps

To a solution of 1.6 g (10 mmol) of 6,7,8,9-Tetrahydro-5H-benzocyclohepten-5-ol in 75 mL of benzene was added p-toluene sulfonic acid (19 mg, 0.1 mmol). The mixture was refluxed overnight using Dean-Stark equipment. After removal of the solvent, the residue was repartitioned between ethyl acetate and water. The organic layers was washed with saturated sodium bicarbonate solution, water and brine and dried over sodium sulfate. Removal of the solvent gave 1.3 g (88%) of 6,7-Dihydro-5H-benzocycloheptene(compound 23,scheme 11).

Provenance & Evidence