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

HRID 359577Notes

Reaction equation

HRID 359577 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.CC(C)=[O:14]>>[OH:14][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1]

Participants

3

Reactant 2

HCID 180Acetone2×HCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

Procedure

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).

Workup

  1. customSolvent was removed on a rotary evaporator
  2. customto give a white crystalline solid (0.1727 g, 99% yield, mp 161-163)

Sources & evidence

ORD record
ord-e3ab7037faa943f087c1cabb13d88545
Source dataset
uspto-grants-1991_03
Patent number
US05001233

Reaction notes

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