1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 10978761, compound

HRID 322793Notes

Reaction equation

HRID 322793 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].[C:13]1([CH3:20])[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1>>[CH3:20][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH2:19][O:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 7929M-Xylene

Product 1

HCID 10978761HCID 10978761, compoundYield 51%

Conditions

Temperature
135.5 °C

Procedure

A mixture of 8.60 g (0.05 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 106.17 g (1.0 mol) of m-xylene under a nitrogen atmosphere is heated at 135-136° C. for 69 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 (3×33 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 3.50 g (51% yield) of a white solid melting at 66-67° 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 (3×33 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-41cc05cf84f94618b560e357f4b1ec84
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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