Hydrochloric Acid → HCID 21249974, compound

Participants

Reaction Steps

18.04 g (132.4 mmol) of freshly melted zinc chloride is added to a solution of 32.46 g (132.4 mmol) of 1-(3-bromo-4-methoxyphenyl)-propan-2-ol and 20.01 g (132.4 mmol) of 4-nitrobenzaldehyde in 166 ml of dry benzene, and then dry hydrogen chloride gas is introduced for 3 hours. The reaction mixture is then heated to boiling for 1 hour and stirred with 150 ml of water. The organic phase is separated and washed in succession with water (2×50 ml), 20% sodium hydrogen sulfite solution (100 ml), 8% sodium bicarbonate solution (50 ml) and water (2×50 ml) and dried. After concentration by evaporation, a thick oil, which during treatment with hot ethanol (450 ml) yields crystalline 6-bromo-3-methyl-7-methoxy-1-(4-nitrophenyl)-isochroman, is obtained: 20.39 g (41%), melting point 128-129° C.

Provenance & Evidence