Toluene → 1,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

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Reaction Steps

In a 2.5 l sulfonating flask with mechanical stirrer, condenser and 500 ml dropping funnel 300 g (7.5 mol) of sodium hydroxide are dissolved in 300 g of water under an argon atmosphere. 750 ml of toluene, 48.4 g (0.15 mol) of tetrabutylammonium bromide and 257 g (1.5 mol) of 4-hydroxy-1,2,2,6,6-pentamethylpiperidine are added. 347 g (3.75 mol) of epichlorohydrin are added dropwise over the course of 1.5 hours at 60° C., and then the mixture is stirred at the same temperature for 4 hours more. The reaction solution is poured into 3 l of ice-water, and the organic phase is separated off, dried over sodium sulfate and concentrated by evaporation. Distillation is carried out over a Vigreux column at 0.05 torr and the fraction having the boiling point 71 to 72° C. is collected.

Provenance & Evidence