Toluene → HCID 11780352, compound

HRID 322797Notes

Reaction equation

HRID 322797 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([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C>[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])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 11780352HCID 11780352, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.58 g (0.015 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 27.64 g (0.30 mol) of toluene under a nitrogen atmosphere is heated in a pressure vessel for 53 hours. The reaction mixture is diluted with diethyl ether and the resultant mixture 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 heptane to give 0.59 g (30% yield) of a white solid melting at 86-87° C.

Workup

  1. temperatureis heated in a pressure vessel for 53 hours
  2. washthe resultant mixture is washed with 10 w/v % ascorbic acid (1×50 mL)
  3. distillationdistilled water (2×50 mL)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customthe volatiles are removed in vacuo
  6. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-d7c6388c5e7e4265ac87d1221181c87e
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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