M-Cresol → (2R,3S,5R)-oxane-2,3,4,5-tetrol

Participants

Reaction Conditions

Reaction Steps

M-cresol (114 g), 3,5-xylenol (42.8 g), diglyme (50.0), and maleic anhydride (3.13 g) were combined in a flask and heated to 95° C. The solution was purged with nitrogen for 3 minutes. Formaldehyde (37.2% in water, 83.7 g) was added slowly over 75 minutes. Heating at 95° C. was continued for four hours. The volatile components were distilled away from the reaction mixture until the residue was at 200° C. Vacuum was applied slowly to the distillation until 35 mmHg and 220° C. were both reached. The novolak resin in the reaction flask was then cooled to room temperature. RMW=9.2; DR=10.4.

Provenance & Evidence