Pentaerythritol → (1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of pentaerythritol (13.6 g, 0.100 mol) in 10 mL of toluene was added freshly distilled triethyl orthoacetate (16.2 g. 18.3 mL, 0.100 mol) and p-toluenesulfonic acid monohydrate (50 mg). The mixture was slowly heated in an oil bath and ethanol was distilled from the mixture over a period of 12 hrs. After removal of the ethanol, the bath temperature was raised to 125° C. and toluene was distilled off until the solution was homogeneous (about 30 mL). The residue was sublimed (bulb to bulb, ~130--C, 2.5 mmHg) to give 4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.21octane (15.0 g, 0.093 mol, 93%).

Provenance & Evidence