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

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Reaction Steps

300 g of sodium hydroxide (7.5 mol) are dissolved in 300 ml of water under an argon atmosphere in a 2.5 l sulfonation flask with a mechanical stirrer, condenser and 500 ml dropping funnel. 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 of epichlorohydrin (3.75 mol) are added dropwise at 60° C. in the course of 1.5 hours and the temperature is then kept at 60° C. for a further 4 hours, while stirring. The reaction solution is poured onto 3 l of ice-water and the organic phase is separated off, dried with sodium sulfate and evaporated. The residue is distilled over a Vigreux column under 0.05 mmHg and the fraction of boiling point 71°-72° C. is collected.

Provenance & Evidence