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

Participants

Reaction Conditions

Reaction Steps

M-cresol (338 g), 3,5-xylenol (229 g), diglyme (625 g), formaldehyde (37.3% in water, 603 g) and oxalic acid (1.13 g) were combined in a 5 liter flask and then heated at 95° C. for one hour. A mixture of m-cresol (338 g) and 3,5-xylenol (229 g) were added to the reaction mixture over one hour. 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=9.0; DR=2.88.

Provenance & Evidence