Dimethyl Sulfoxide → 3-Chloro-2-methoxymethoxy-2'-methoxymethoxybenzophenone

A solution of 16.0 ml of oxalyl chloride in 500 ml of dichloromethane was placed in a 1 1 flask and cooled with a dry ice-acetone bath. Dimethyl sulfoxide (14.0 ml) was added dropwise with stirring over a 10 min period. After a 40 min reaction period, a solution of 51.0 g of (3-chloro-2-methoxymethoxyphenyl)(2-methoxymethoxyphenyl)methanol in 120 ml of dichloromethane was added dropwise over a 45 min period with stirring at about -78° C. and allowed to react another 45 min. An orange suspension formed. Triethylamine (50 ml) was added and the slurry was swirled occasionally and was allowed to warm to room temperature. The slurry was diluted with 1 1 of ether and the resulting mixture was extracted with 3-300 ml portions of water, 300 ml of 2 percent hydrochloric acid, and 200 ml of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 50.5 g of the title compound as a viscous pale orange-tinted oil. The proton and carbon NMR spectra were consistent with the assigned structure.

1. temperaturecooled with a dry ice-acetone bath
2. customAfter a 40 min reaction period
3. stirringwith stirring at about -78° C.
4. customto react another 45 min
5. customAn orange suspension formed
6. extractionthe resulting mixture was extracted with 3-300 ml portions of water, 300 ml of 2 percent hydrochloric acid, and 200 ml of saturated aqueous sodium bicarbonate
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated by evaporation under reduced pressure

ORD record

ord-9f9b91214df846b39141ae7355260109

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04999448