Vinyl Acetate → 12-Acetoxy-2-chloro-9-formyl-9,10-dihydro-9,10-ethanoanthracene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-9-anthraldehyde, prepared as in Example 1c, (100.0 g, 0.415 moles) and vinyl acetate (400 ml, 374 g, 4.34 moles) was placed in a stainless steel bomb (PARR) and heated at 200° C. (sand bath temp.) for 24 h, then cooled. The reaction mixture was concentrated on the rotary evaporator to remove the excess vinyl acetate, leaving the crude product as a tan crystalline solid. The crude product from several batches, which consumed 670.0 g (2.78 moles) of 2-chloro-9-anthraldehyde, was pooled. Trituration with diethyl ether (1.0 L) gave an off-white crystalline solid which was collected by filtration, washed with diethyl ether (2×300 ml), then vacuum dried to afford 629.0 g (69.1%) of the title compound (mp 145°-153° C.).

Provenance & Evidence