Dimethylformamide → 6-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 637900Notes

Reaction equation

HRID 637900 reaction equation
CN(C)[CH:3]=[O:4].[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[C:27]([OH:28])=[C:26]([O:29][CH3:30])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1C)(=[O:8])[CH3:7]>O=O.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[C:27](=[O:28])[C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[C:3](=[O:4])[C:23]=1[CH3:24])(=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 130652366-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128814656-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (20 ml) of 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methylphenol (1.1 g) is added bis(salicylidene)ethylenediiminocobalt(II) (40 mg) and the mixture is stirred in oxygen streams at atmospheric pressure and temperature for 72 hours. The product is isolated as in Example 7 and recrystallized from etherhexane (1:1). The above procedure yields 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (0.84 g) as orange-yellow needles melting at 47° C.

Workup

  1. customThe product is isolated as in Example 7
  2. customrecrystallized from etherhexane (1:1)

Sources & evidence

ORD record
ord-9d0c04129eaa4c1dac08bb09ea2adde5
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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