tert-Butanol → 1-(2,3-Dihydroxy-propyl)-cyclohexane-1,3-dicarboxylic acid diethyl ester

Participants

Reaction Steps

To a solution of 1-allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester from step 2 (250 g, 0.93 mol) in t-butanol (2.3 L) and water (2.3 L) was added potassium ferricyanide (920 g, 2.79 mol), potassium carbonate (386 g, 2.79 mol), potassium osmate dihydrate (4.75 g, 13 mmol) and quinuclidine (0.073 g, 7.0 mmol). The resulting dark colored solution was stirred at rt overnight and then quenched with portion-wise addition of sodium sulfite (1.05 kg, 8.37 mol). After dilution with ethyl acetate, it was extracted, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue (224 g) was used in the next step without delay and without further purification.

Provenance & Evidence