Pyridine → 6-(12-Hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 637899Notes

Reaction equation

HRID 637899 reaction equation
CN(C)[CH:3]=[O:4].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[C:24]([OH:25])=[C:23]([O:26][CH3:27])[C:22]([O:28][CH3:29])=[CH:21][C:20]=1C.N1C=CC=CC=1>O=O>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[C:24](=[O:25])[C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[C:3](=[O:4])[C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6228DimethylformamideHCID 202546266-(12-Hydroxydodecyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128814646-(12-Hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (30 ml) of 6-(12-hydroxydodecyl)-2,3-dimethoxy-5-methylphenol (1.7 g) are added pyridine (50 mg) and bis(4-hydroxysalicylidene)ethylenediiminocobalt(II) (36 mg), and the mixture is stirred in oxygen streams at atmospheric temperature and pressure for 72 hours. The reaction product is isolated as in Example 7 and recrystallized from ether. The above procedure yields 6-(12-hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.37 g), m.p. 63° C.

Workup

  1. customThe reaction product is isolated as in Example 7
  2. customrecrystallized from ether

Sources & evidence

ORD record
ord-ebdab80d517442d08aab9fde241433e4
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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