Methanol → 2,6-Dimethoxy-4-tert-butylphenol

HRID 427114

Reaction equation

[Na].Br[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5](Br)[C:4]=1[OH:14].CN(C)[CH:17]=[O:18].[CH3:20][OH:21]>>[CH3:20][O:21][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([O:18][CH3:17])[C:4]=1[OH:14]

Participants

Reactant 4

HCID 887Methanol

HCID 6228Dimethylformamide

HCID 2525182,6-Dibromo-4-tert-butylphenol

HCID 5360545Sodium

Product 1

HCID 106560602,6-Dimethoxy-4-tert-butylphenolYield 89%

Procedure

Sodium (18.2 g, 0.79 g atom) was dissolved in methanol (152 ml). 2,6-Dibromo-4-t-butylphenol (30 g), cuprous bromide (4 g, 0.028 mole) and dimethylformamide (152 ml) were added and the mixture boiled under reflux (88°-84° C.) with stirring for 2 hours. Work up as given in Example 1 gave 2,6-dimethoxy-4-t-butylphenol as a pale yellow oil, 19.9 g of 90% purity (89% yield).

Workup

temperatureunder reflux (88°-84° C.)

Sources & evidence

ORD record: ord-6fe12f57d5874c38900fc4544c6abd6e
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172960

Linked notes

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