Isolongifolanone- parent → HCID 68161955, compound

Participants

Reaction Conditions

Reaction Steps

A 5 L reaction vessel was charged with 1,1,5,5-tetramethyl-hexahydro-2,4-a-methano-naphthalen-8-one (440 g, 2.0 mol) (commercially available at IFF), formamidine acetate (1040 g, 10.0 mol) and butanol (2 L). The reaction mixture was heated to 120° C. for 10 hours and then cooled to 25° C. The reaction mixture was washed twice with brine (1 L) and purified by vacuum distillation to afford crude product 6,6,10,10-tetramethyl-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzo[H]quinazoline (430 g) having a boiling point of 159° C. at a pressure of 1.0 mmHg. Further recrystallization from ethanol afforded 6,6,10,10-tetramethyl-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzo[H]quinazoline (95% purity) (125 g) with a melting point of 44-45° C.

Provenance & Evidence