Red-Al → HCID 69323130, compound

Participants

Reaction Conditions

Reaction Steps

A 1-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (260 g, 0.84 mol) and toluene (260 g). The resulting mixture was stirred at 20° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-4-methyl-cyclohex-3-enecarbaldehyde (275 g, 1.16 mol, synthesized as above in EXAMPLE V) was added over about 2 hours. The temperature was allowed to rise to 40° C. The reaction mass was aged for 3 hours. The excessive Vitride reagent was quenched with ethyl acetate (22 g), followed by sodium hydroxide (25%, 134 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-4-methyl-cyclohex-3-enyl]-methanol (250 g, 0.96 mol).

Provenance & Evidence