Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 423242Notes

Reaction equation

HRID 423242 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Procedure

To a solution of 3-fluoro-4-hydroxybenzoic acid (3.0 g) in methanol (30 mL) was added conc. sulfuric acid (3 mL), and the mixture was heated for 5 hours under reflux. The reaction solution was allowed to stand for cooling down to room temperature, and then concentrated in vacuo. The residue was diluted with ethyl acetate, washed successively with water, saturated aqueous sodium bicarbonate, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (2.99 g).

Workup

  1. temperaturethe mixture was heated for 5 hours
  2. temperatureunder reflux
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed successively with water, saturated aqueous sodium bicarbonate, water, and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4085a158c977440c8dadfa70b6796d93
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…