Hydrochloric Acid → Methyl 2-fluoro-4-hydroxybenzoate

HRID 50148Notes

Reaction equation

HRID 50148 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-6ac0ac70dd644ad5998999e03e31ff24
Source dataset
uspto-grants-2004_03
Patent number
US06710208B2

Reaction notes

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