Bromhydrol → 4-Hydroxy-4'-(2-methyloctanoyl) biphenyl

Participants

Reaction Conditions

Reaction Steps

Then, 400 mg (1.2 mmol) of the above 4-methoxy-4'-(2-methyloctanoyl) biphenyl was dissolved in 6 ml of dried toluene in a flask of 50 ml. After the solution was added with 1.3 g (5.0 mmol) of aluminum bromide under ice cooling for 5 minutes, the resulting mixture was stirred under ice cooling for 6 hours, at room temperature for about 60 hours and at 40° C. for 11 hours. After the completion of the reaction, the resulting product was poured into 100 ml of ice water together with 40 ml of toluene. After the separation into two layers, the organic layer was taken out, and the extraction with 40 ml of toluene on aqueous layer was repeated two times. Thereafter, the organic layers were gathered, washed with 40 ml of water and dried on anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the product was concentrated and purified through a silica gel column (toluene→toluene: diethyl ether=5:1 (v/v)] to obtain 200 mg (yield: 54%) of a reddish brown oily substance of 4-hydroxy-4'-(2-methyloctanoyl) biphenyl having the following properties:

Provenance & Evidence