4-Hydroxy-2,2,6,6-tetramethylpiperidine → HCID 19073315, compound

Participants

Reaction Steps

A round-bottomed flask, equipped with magnetic stirrer and condenser, is charged with 833 g (5.30 mol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 418 g (1.05 mol) of 2-butyne-1,4-diol-ditosylate [C.A. Registry No. 6337-59-3] in 3.6 1 of acetonitrile under argon. The reaction mixture is refluxed overnight, then cooled, poured on ice and extracted repeatedly with ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from ethanol gives 295 g (76%) of 1,4-bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)but-2-yne (209), m.p. 203.4° C., in the form of white crystals.

Provenance & Evidence