Methanol → Methyl 2-fluoro-4-hydroxybenzoate

HRID 404334Notes

Reaction equation

HRID 404334 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 22463192Methyl 2-fluoro-4-hydroxybenzoateYield 85%

Conditions

Temperature
80 °C

Procedure

To a round bottom containing 2-fluoro-4-hydroxybenzoic acid (Commercially available from TCI America) (5.34 g, 34.19 mmol) was added a cold solution of MeOH (50 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 residue was diluted with diethyl ether. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield T7.1 as a white solid (5.82, 85% yield). 1H NMR (400 MHz, DMSO-d6) 10.79 (1H, s), 7.75 (1H, t, J=8.8 Hz), 6.69 (1H, dd, J=8.6, 2.3 Hz), 6.62 (1H, dd, J=13.1, 2.2 Hz), 3.78 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-7d01e7b5434b4068bfdf50d126050e0c
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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