Red-Al → HCID 69324125, compound

Participants

Reaction Conditions

Reaction Steps

A 3-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (1112 g, 3.5 mol) and toluene (1 Kg). The resulting mixture was stirred at 21.2° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2,4-dimethyl-cyclohex-3-enecarbaldehyde (778.5 g, 2.59 mol, synthesized as above in EXAMPLE XI) was added over about 4 hours. The temperature was allowed to rise to 35° C. The reaction mass was aged for 1 hour. The excessive Vitride reagent was quenched with ethyl acetate (125 g), followed by sodium hydroxide (30%, 3 Kg). The temperature was allowed to rise to 40° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and distilled to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2,4-dimethyl-cyclohex-3-enyl]-methanol (829.5 g).

Provenance & Evidence