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

Participants

Reaction Conditions

Reaction Steps

64.0 g of sodium hydroxide (1.6 mol) are dissolved in 64 ml of water under argon in a 750 ml sulfonation flask fitted with mechanical stirrer, condenser, thermometer and 100 ml dropping funnel. 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. 8.8 g (636 mmol) of epichlorohyrdin 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 poured into 11 of ice water, and the organic phase is separated off, dried using sodium sulfate and evaporated on a rotary evaporator. The residue is distilled at 8×103 mmHg. Boiling point: 48° C., yield: 28 g (41%). GC: 98 %.

Provenance & Evidence