1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 10912826, compound

HRID 322799Notes

Reaction equation

HRID 322799 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1>ClC1C=CC=CC=1>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 7809P-Xylene

Product 1

HCID 10912826HCID 10912826, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 8.60 g (0.1 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 53.09 g (0.5 mol) of p-xylene in 61 mL of chlorobenzene under a nitrogen atmosphere is heated at 140° C. for 56 hours. The reaction mixture is filtered to remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, and the filtrate is washed with 10 w/v % ascorbic acid (3×30 mL) and distilled water (2×50 mL). The organic phase is dried over anhydrous sodium sulfate and the volatiles are removed in vacuo. The residue is recrystallized from heptane to give 3.33 g (48% yield) of the title compound as a white solid melting at 92.5-93° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine
  3. washthe filtrate is washed with 10 w/v % ascorbic acid (3×30 mL)
  4. distillationdistilled water (2×50 mL)
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. customthe volatiles are removed in vacuo
  7. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-36280be0a63e4dafa7c16e226797ab21
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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