4-Bromo-3,5-dihydroxybenzoic acid → 4-O-methylgallic acid

HRID 427116Notes

Reaction equation

Br[C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12].[CH3:13][O-:14].[Na+]>>[CH3:13][O:14][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12]

Participants

Reactant 2

HCID 860234-Bromo-3,5-dihydroxybenzoic acid

HCID 10942334Sodium Methoxide

Product 1

HCID 780164-O-methylgallic acidYield 45%

Procedure

Treatment of 4-bromo-3,5-dihydroxybenzoic acid (23.3 g, 0.1 mole) with sodium methoxide (18.5 g, 0.8 g atom) in an analogous procedure to that of Example 9 with a 9 hour reflux yielded 12 g (theory 18.4 g) of a white solid, m.p 238°-42° C. NMR showed this to be 45% title product and 55% starting material.

Workup

customyielded 12 g (theory 18.4 g) of a white solid, m.p 238°-42° C

Sources & evidence

ORD record: ord-3f1a7654c5974f109e3199dc36d0cdd2
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172960

Reaction notes

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