2,6-Dibromophenol → 2,6-Dimethoxyphenol

HRID 427115

Reaction equation

HRID 427115 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[C:3]=1[OH:9].[CH3:10][O-:11].[Na+].BrC1C=C(C(C)(C)C)C=C(Br)[C:15]=1[OH:25]>CO.CN(C)C=O>[CH3:10][O:11][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:25][CH3:15])[C:3]=1[OH:9]

Participants

6

Reactant 3

HCID 118472,6-DibromophenolHCID 2525182,6-Dibromo-4-tert-butylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 70412,6-Dimethoxyphenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2,6-Dibromophenol (14.5 g, 0.058 mole) was treated with sodium methoxide (from 10.3 g sodium, 0.45 g atom) in methanol (100 ml) and dimethylformamide (100 ml) in the presence of cuprous iodide (2 g) in the same way as described in detail for 2,6-dibromo-4-t-butylphenol in Example 9. The crude yield of title product was 5.4 g (60%), m.p. 53°-6° C. (literature gives 55°-6° C.). The lower yield may be explained by incomplete extraction, 2,6-dimethoxyphenol being to some extent water soluble.

Sources & evidence

ORD record
ord-a1584fb037014287b1d94158ab4f23a8
Source dataset
uspto-grants-1979_10
Patent number
US04172960

Linked notes

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