Hydrochloric Acid → Methyl 2-fluoro-4-hydroxybenzoate

HRID 1937035Notes

Reaction equation

HRID 1937035 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:16]O>>[CH3:16][O:6][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 224632172-Fluoro-4-(methoxymethoxy)-benzoic acid

Product 1

HCID 22463192Methyl 2-fluoro-4-hydroxybenzoateYield 100%

Procedure

To a solution of 2-fluoro-4-methoxymethoxybenzoic acid (19.9 g, 100 mmol) in methanol (200 ml) is added conc. hydrochloric acid solution (0.5 ml, catalytic). The solution is heated at reflux overnight. The solution is evaporated in vacuo to give an off-white solid (16.9 g, 100%). δH (300 MHz, CD3OD) 3.83 (3H, s), 6.52 (1H, dd, J=2.3, 12.9 Hz), 6.63 (1H, dd, J=2.1, 8.5 Hz), 7.78 (1H, t, J=8.7 Hz); δC (75 MHz, CD3OD); m/z 170 [(M+), 10%], 139 [(M-OMe)+, 10%]52.34, 104.30, 104.34, 110.78, 112.48, 134.61, 134.96, 163.36, 163.61, 164,93, 165.03, 165.09, 165.19, 166.38, 166.46, 166.79, 167.03, 167.60, 167.65, 205.58.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux overnight
  3. customThe solution is evaporated in vacuo

Sources & evidence

ORD record
ord-660ffab30c854080b3cba4788cca6b54
Source dataset
uspto-grants-2002_05
Patent number
US06392010B1

Reaction notes

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