Benzene → Benzophenone

Temperature

0 °C

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.

1. additionAfter addition
2. temperaturethe resulting mixture was heated to 25° C.
3. customAfter a reaction
4. distillationthe solvent and an excess of oxalyl chloride were distilled off under reduced pressure
5. dissolutionThe obtained residue was dissolved in 450 ml of tetrahydrofuran
6. temperaturecooled to −50° C
7. additionAfter addition
8. temperaturethe resulting mixture was heated to 25° C.
9. stirringstirred for 4 hours
10. additionwas added
11. washthe reaction solution was washed with water
12. customthe solvent was removed
13. customthe obtained product was purified

ORD record

ord-444b4628d7c84f9e862dd139f5558328

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08709308B2