Toluene → 2,2,6,6-Tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

Participants

Reaction Conditions

Reaction Steps

In a 750 ml sulfonating flask with mechanical stirrer, condenser and 100 ml dropping funnel 64.0 g (1.6 mol) of sodium hydroxide are dissolved in 64 ml of water under an argon atmosphere. 170 ml of toluene, 10.3 g (31.8 mmol) of tetrabutylammonium bromide and 50 g (318 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine are added. 58.8 g (636 mmol) of epichlorohydrin are added dropwise at 45° C. The mixture is then stirred at 50° C. for 4 hours. The reaction mixture is cooled to room temperature and then poured into 1 l of ice-water, the organic phase is separated off and dried over sodium sulfate, and the residue is concentrated on a rotatory evaporator. The residue is distilled at 8·10-3 torr. Boiling point: 48° C.

Provenance & Evidence