Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 1662438Notes

Reaction equation

HRID 1662438 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>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

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

Product 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoateYield 87%

Conditions

Temperature
80 °C

Procedure

To a round bottom flask containing 3-fluoro-4-hydroxybenzoic acid (5.03 g, 32.22 mmol) (commercially available from Aldrich) was added a cold solution of MeOH (50.0 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the mixture was diluted with diethyl ether. The organic phase was washed carefully twice with saturated aqueous NaHCO3 and once with brine. The organic phase was then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford 66.49A as a white solid (4.79 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (2H, m), 7.06 (1H, t, J=8.4 Hz), 5.62 (1H, d, J=4.3 Hz), 3.91 (3H, s).

Workup

  1. customthe solvent was removed
  2. additionthe mixture was diluted with diethyl ether
  3. washThe organic phase was washed carefully twice with saturated aqueous NaHCO3 and once with brine
  4. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-48f915c9b9554be488efd4304c4e34ad
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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