Acetone → 1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

Participants

Reaction Steps

In a 100 ml flask, a solution of 0.047 M DMD in acetone (21.2 ml, 1 mmol) was added to a cold stirred solution of 2,2,6,6-tetramethyl-4-piperidinol (0.1572 g, 1 mmol) in acetone (10 ml). The reaction mixture was stirred for two hours in an ice bath. Solvent was removed on a rotary evaporator to give a white crystalline solid (0.1727 g, 99% yield, mp 161-163). Sublimation on the Kugelrohr (110-120°, 1×10-4 mmHg) gave white needles (0.170 g). Measured mp was 162-163; reported mp is 155-159 (Lee et al 1975 and Rozantsey et al 1966).

Provenance & Evidence