Benzene → Benzophenone

Participants

Reaction Conditions

Reaction Steps

90.0 g (381.8 mmol) of a benzene compound represented by the above formula (8) was dissolved in 450 ml of dichloromethane and cooled to 0° C. 148.8 g (1145.4 mmol) of oxalyl chloride and 4 ml of N,N-dimethylformamide were added dropwise to this solution. After addition, the resulting mixture was heated to 25° C. and stirred for 2 hours. After a reaction, the solvent and an excess of oxalyl chloride were distilled off under reduced pressure. The obtained residue was dissolved in 450 ml of tetrahydrofuran and cooled to −50° C. 172 ml (343.6 mmol) of phenylmagnesium bromide (2.0M diethyl ether solution) was added dropwise to this solution. After addition, the resulting mixture was heated to 25° C. and stirred for 4 hours. After a reaction, 200 ml of toluene was added, the reaction solution was washed with water, the solvent was removed, and the obtained product was purified by reslurrying with methanol to obtain a benzophenone derivative represented by the following formula (27) as 73.3 g (214.5 mmol, yield of 56%) of a white solid.

Provenance & Evidence