Red-Al → HCID 69322502, 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 (226 g, 0.73 mol) and toluene (226 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)-cyclohex-3-enecarbaldehyde (310 g, 1.32 mol, synthesized as above in EXAMPLE II) was added over about 2 hours. The temperature was allowed to rise to 45° C. The reaction mass was aged for 2.5 hours. The excessive Vitride reagent was quenched with ethyl acetate (CH3CO2CH2CH3, 44 g), followed by sodium hydroxide (NaOH, 25%, 467 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was diluted with toluene (100 mL), washed with hot water (1 L) twice, and then concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohex-3-enyl]-methanol (390 g) having a boiling point of 153° C. at a pressure of 1.7 mmHg.

Provenance & Evidence