Methanol → Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl ester

HRID 1177183Notes

Reaction equation

HRID 1177183 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12].OS(O)(=O)=O.[CH3:18]O>>[CH3:18][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([OH:11])[C:2]([Br:1])=[C:3]([OH:12])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 860234-Bromo-3,5-dihydroxybenzoic acid

Product 1

HCID 118602Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl esterYield 94%

Procedure

To a solution of 4-bromo-3,5-dihydroxy-benzoic acid (450 g, 1.94 mol) in MeOH (3.5 L) was added drop wise conc. H2SO4 (20 mL) at room temperature, and the mixture was refluxed overnight. TLC (petroleum ether/EtOAc=1/1) showed the reaction was complete. MeOH was removed under vacuum to about 250 mL and the resulting solid was filtered. The filter cake was dried under vacuum to give the title compound (450 g, 94% yield) as a white solid

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customMeOH was removed under vacuum to about 250 mL
  3. filtrationthe resulting solid was filtered
  4. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-1e45b7d4cce34195b9eecf6d5cfe4171
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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