4-Methylbenzoyl Chloride → Benzophenone, 4-chloro-4'-methyl-

Temperature

80 °C

An 80° C. stirred solution of p-toluoyl chloride (10.0 g, 64.7 mmol) in chlorobenzene (15 ml) was treated in portions with aluminum chloride (8.63 g, 64.7 mmol) over 20 minutes. The mixture was stirred 15 hours at 80° C., cooled, and quenched by addition of ice-water and concentrated hydrochloric acid (10 ml). The mixture was extracted twice with diethyl ether and once with a small volume of dichloromethane. The combined extracts were washed with water, 10% (w/v) aqueous sodium hydroxide, and water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The residue was dissolved in boiling n-hexane, treated with activated charcoal, and filtered hot. The filtrate was cooled and the product was collected by filtration and dried to provide 7.57 g (51%) of 4-(4-chlorobenzoyl) toluene, m.p. 122°-123° C.

1. temperaturecooled
2. customquenched by addition of ice-water and concentrated hydrochloric acid (10 ml)
3. extractionThe mixture was extracted twice with diethyl ether and once with a small volume of dichloromethane
4. washThe combined extracts were washed with water, 10% (w/v) aqueous sodium hydroxide, and water
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated to dryness under vacuum
7. dissolutionThe residue was dissolved
8. additiontreated with activated charcoal
9. filtrationfiltered hot
10. temperatureThe filtrate was cooled
11. filtrationthe product was collected by filtration
12. customdried

ORD record

ord-c7280690f5ec40f889dcad19cc52b594

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04590201