Dimethylformamide → 2-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

HRID 637903

Reaction equation

HRID 637903 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][C:20]1[C:25]([O:26]C2CCCCO2)=[C:24]([O:33][CH3:34])[C:23]([O:35][CH3:36])=[CH:22][C:21]=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][C:20]1[C:25](=[O:26])[C:24]([O:33][CH3:34])=[C:23]([O:35][CH3:36])[C:3](=[O:4])[C:21]=1[CH3:22])(=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 542535796-(10-Acetoxydecyl)-2,3-dimethoxy-5-methyl-1-tetrahydropyranyloxybenzene

Product 1

HCID 110902052-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (20 ml) of 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-1-tetrahydropyranyloxybenzene (240 mg) is added bis(salicylidene)ethylenediiminocobalt(II) (14 mg), followed by stirring in oxygen streams at atmospheric temperature and pressure for 72 hours. The reaction product is isolated in the same manner as Example 7 and recrystallized from hexane. The above procedure yields 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (110 mg) as orange-yellow needles melting at 37° C.-38° C.

Workup

  1. customThe reaction product is isolated in the same manner as Example 7
  2. customrecrystallized from hexane

Sources & evidence

ORD record
ord-7474d7c359fc4397a464544cc8e4e99c
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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