Methanol → Methyl 4-hydroxy-3-(trifluoromethyl)benzoate

HRID 423251Notes

Reaction equation

HRID 423251 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Product 1

HCID 13962148Methyl 4-hydroxy-3-(trifluoromethyl)benzoate

Procedure

To a solution of 4-hydroxy-3-trifluoromethylbenzoic acid (395 mg) in methanol (5 mL) was added conc. sulfuric acid (0.4 mL), and the mixture was heated for 6 hours under reflux. The reaction mixture was allowed to stand for cooling down to room temperature, and concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine, and concentrated to give the title compound (403 mg).

Workup

  1. temperaturethe mixture was heated for 6 hours
  2. temperatureunder reflux
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water and saturated brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f265ef553384a79ace74b33c928e34a
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…