3-Methylbenzoyl chloride → 4-Chloro-3'-methylbenzophenone

Temperature

80 °C

A stirred solution of m-toluoyl chloride (10.0 g, 64.7 mmol) in chlorobenzene (13.2 ml) at 80° C. was treated with aluminum chloride (8.63 g, 64.7 mmol) in portions over 30 minutes. The mixture was stirred 15 hours at 80° C., cooled to ambient temperature, stirred 16 hours, and quenched by addition of ice and concentrated hydrochloric acid (5.0 ml). The mixture was extracted three times with dichloromethane, and the combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was dissolved in boiling n-hexane, treated with activated charcoal, filtered, and cooled. The product was filtered and dried to provide 9.15 g of 3-(4-chlorobenzoyl) toluene. The filtrate was concentrated under vacuum and filtered to provide an additional 0.28 g of product. Total yield was 9.42 g (63%), m.p. 103°-105° C.

1. temperaturecooled to ambient temperature
2. stirringstirred 16 hours
3. customquenched by addition of ice and concentrated hydrochloric acid (5.0 ml)
4. extractionThe mixture was extracted three times with dichloromethane
5. washthe combined extracts were washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under vacuum
8. dissolutionThe residue was dissolved
9. additiontreated with activated charcoal
10. filtrationfiltered
11. temperaturecooled
12. filtrationThe product was filtered
13. customdried

ORD record

ord-340d8640290749e8ad491db42c6a6aeb

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04590201