M-Xylene → HCID 11036315, compound

HRID 322795Notes

Reaction equation

HRID 322795 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].[C:21]1([CH3:28])[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1>>[C:11]([O:10][CH:5]1[CH2:6][C:7]([CH3:9])([CH3:8])[N:2]([O:1][CH2:28][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[C:3]([CH3:20])([CH3:19])[CH2:4]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7929M-XyleneHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 11036315HCID 11036315, compoundYield 59%

Procedure

A mixture of 13.77 g (0.05 mol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine and 106.17 g (1.0 mol) of m-xylene under a nitrogen atmosphere is heated at reflux for 50 hours. The reaction mixture is filtered to remove the hydroxylamine, and the filtrate is washed with 10 w/v % ascorbic acid (1×50 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 isopropyl alcohol to give 5.62 g (59% yield) of a white solid melting at 64-65° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 50 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the hydroxylamine
  5. washthe filtrate is washed with 10 w/v % ascorbic acid (1×50 mL)
  6. distillationdistilled water (2×50 mL)
  7. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  8. customthe volatiles are removed in vacuo
  9. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-76fec14ef3744b5a96ce37aa8ac8bd38
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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