Epichlorohydrin → 1-(Cyclohexyloxy)-2,2,6,6-tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

Participants

Reaction Steps

78.4 g (1.96 mol) of sodium hydroxide are dissolved in 80 ml of water under argon in a 750 ml sulfonation flask fitted with stirrer, thermometer and dropping funnel. 100 g (392 mmol) of 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine and 12.6 g (39.2 mmol) of tetrabutylammonium bromide dissolved in 250 ml of toluene are added. The mixture is warmed to 50°-55° C., and 90.7 g (980 mmol) of epichlorohydrin are added dropwise over the course of 45 minutes, during which the mixture is stirred vigorously. The mixture is stirred at 55° C. for a further 3 hours and then poured into 1 litre of ice water, and the organic phase is separated off and washed once with water. The organic phase is dried over sodium sulfate, decoloured using activated charcoal, filtered and evaporated. The residue is distilled over a Vigreux column: boiling point 116°-117° C./0.06 mmHg.

Provenance & Evidence