Chrysene → 1-Chrysen-6-ylethanone

Participants

Reaction Steps

Friedel-Crafts reaction of chrysene with AlCl3 /CH3COCl/PhNO2 gave a mixture of 2-, 3-, and 6-acetylchrysenes (285 g, Cambridge Chemical, Inc.). This was stirred and heated in CH2Cl2 (400 mL) and then filtered. The insoluble material, 2-acetylchrysene, was washed copiously with CH2Cl2. The solvent was removed from the filtrate. The resulting solid was dissolved in PhCH3, then the mixture containing the remaining two isomers chromatographed using PhCH3 as eluting solvent on a plug of SiO2 (1 kg). The faster eluting isomer is 6-acetylchrysene while the slower is 3-acetylchrysene. The chromatography gave 132 g of impure 6-acetylchrysene, and 76 g of impure 3-acetylchrysene. These materials were used without further purification. Pure samples of the compounds were obtained by preparative HPLC using PhCH3 as the eluting solvent.

Provenance & Evidence