Methanol → 6-(9-Acetoxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 637902

Reaction equation

HRID 637902 reaction equation
C[OH:2].[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21]([OH:22])=[C:20]([O:23][CH3:24])[C:19]([O:25][CH3:26])=[CH:18][C:17]=1[CH3:27])(=[O:5])[CH3:4].N1C=CC=CC=1>O=O.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:2])[C:17]=1[CH3:27])(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 202546186-(9-Acetoxynonyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128326566-(9-Acetoxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 977OxygenSolvent

Procedure

To a methanol solution (30 ml) of 6-(9-acetoxynonyl)-2,3-dimethoxy-5-methylphenol (1.1 g) are added pyridine (0.3 ml) and 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 as in Example 7 and recrystallized from hexane. The above procedure yields 6-(9-acetoxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as orange-yellow needles melting at 30° C.

Workup

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

Sources & evidence

ORD record
ord-3c87245a2018404ab9216db4a6de9955
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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