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 the addition, the resulting mixture was heated to 25° C. and stirred for 2 hours. After the 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 phenyl magnesium bromide (2.0 M diethyl ether solution) was added dropwise to this solution. After the addition, the resulting mixture was heated to 25° C. and stirred for 4 hours. After the reaction, 200 ml of toluene was added, the reaction product was washed in 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 (22) as 73.3 g (248.1 mmol, yield rate of 65%) of a white solid.

1. additionAfter the addition
2. temperaturethe resulting mixture was heated to 25° C.
3. customAfter the 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 the addition
8. temperaturethe resulting mixture was heated to 25° C.
9. stirringstirred for 4 hours
10. additionwas added
11. washthe reaction product was washed in water
12. customthe solvent was removed
13. customthe obtained product was purified

ORD record

ord-fd0db5e3ddd445098984444f02bcdfca

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691120B2