2,5-Dimethoxybenzoic acid → 5-Hydroxy-2-methoxybenzoic acid

HRID 1361623Notes

Reaction equation

HRID 1361623 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>S(=O)(=O)(O)O>[OH:12][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 760272,5-Dimethoxybenzoic acid

Product 1

HCID 184646075-Hydroxy-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,5-dimethoxybenzoic acid (10.0 g, 54.9 mmol) in 55 mL concentrated sulfuric acid was heated to 55 deg. C. for 48 h. The reaction was then poured into ice. A precipitate formed, and the mixture was allowed to stand overnight. The resulting crystals were collected by filtration and dried in vacuo. The material was further purified by silica gel chromatography to give 5-hydroxy-2-methoxybenzoic acid as a white solid. MS m/z=169.0 [M+1]+. Calc'd for C8H8O4: 168.15.

Workup

  1. additionThe reaction was then poured into ice
  2. customA precipitate formed
  3. waitto stand overnight
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried in vacuo
  6. customThe material was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd809b9f7e984f4e833163ab51eb972e
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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