Chloranil → HCID 11460899, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of the hexahydropentacene (221.78 g, 0.720 mol), chloranil (362.6 g, 1.475 mol) and 4 L toluene is kept at reflux for 2½h. The mixture is cooled to about 50° C. and 350 mL 33% sodium hydroxide solution is gradually added. The organic layer is separarted, while the aquous layer is washed with toluene. The combined toluene layers are filtered over aluminium oxide and are rotary evaporated. The residue is stirred with a mixture of 500 mL toluene and heptane. Filtration and washing gives 188.0 g of the product (0.618 mol, 86%). 1H-NMR (CDCl3): δ 5.35 (dd, 2H), 7.05 (dd, 2H), 7.4 (m, 4H), 7.75 (m, 8H).

Provenance & Evidence