Dimethylformamide → 2,3-Dimethoxy-5-methyl-1,4-benzoquinone

HRID 637906Notes

Reaction equation

HRID 637906 reaction equation
CN(C)C=[O:4].[CH3:6][O:7][C:8]1[C:14]([O:15][CH3:16])=[C:13]([O:17]C)[CH:12]=[C:11]([CH3:19])[C:9]=1N>O=O.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[CH3:16][O:15][C:14]1[C:13](=[O:17])[CH:12]=[C:11]([CH3:19])[C:9](=[O:4])[C:8]=1[O:7][CH3:6]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 543331362,3,4-Trimethoxy-6-methyl aniline

Product 1

HCID 690682,3-Dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (35 ml) of 2,3,4-trimethoxy-6-methyl aniline (3.4 g) is added bis(salicylidene)ethylenediiminocobalt(II) (120 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 2,3-dimethoxy-5-methyl-1,4-benzoquinone (2.9 g) as orange-yellow needles melting at 59° C.-60° C.

Workup

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

Sources & evidence

ORD record
ord-034c617fea1648cfb125fb72280d7937
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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