Oxygen → 6-(9-Hydroxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 637897

Reaction equation

HRID 637897 reaction equation
ClCCl.[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[C:19]([OH:20])=[C:18]([O:21][CH3:22])[C:17]([O:23][CH3:24])=[CH:16][C:15]=1[CH3:25].N1C=CC=CC=1.[O:32]=O>C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[C:19](=[O:20])[C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:16](=[O:32])[C:15]=1[CH3:25]

Participants

6

Reactant 4

HCID 977OxygenHCID 1049PyridineHCID 6344DichloromethaneHCID 202546256-(9-Hydroxynonyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128814626-(9-Hydroxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 26517SalcomineCatalyst

Procedure

To a dichloromethane solution (30 ml) of 6-(9-hydroxynonyl)-2,3-dimethoxy-5-methylphenol (1.8 g) are added pyridine (0.5 ml) and bis(salicylidene)ethylenediiminocobalt(II) (32 mg). The mixture is stirred in oxygen streams at atmospheric temperature and pressure. The reaction product is isolated as in Example 7 and recrystallized from hexane. The above procedure yields 6-(9-hydroxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.2 g) as orange-yellow needles melting at 45° C.

Workup

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

Sources & evidence

ORD record
ord-af561fe4b32b46d3a0de5c951aca70e5
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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