Methanol → Methyl 2,6-difluoro-4-hydroxybenzoate

HRID 82784Notes

Reaction equation

HRID 82784 reaction equation
O=S(Cl)Cl.[F:5][C:6]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([F:16])[C:7]=1[C:8]([OH:10])=[O:9].[CH3:17]O>>[F:5][C:6]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([F:16])[C:7]=1[C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27787762,6-difluoro-4-Hydroxybenzoic Acid

Product 1

HCID 22087431Methyl 2,6-difluoro-4-hydroxybenzoateYield 99%

Procedure

SOCl2 (4.16 g, 30.1 mmol) was added to a solution of 2,6-difluoro-4-hydroxybenzoic acid (1.50 g, 8.62 mmol) in MeOH (20 mL) and the resulting mixture was heated at reflux for 24 h. After cooling the solvent was removed in vacuo to give the title compound (1.62 g, 99%) as a white crystalline solid; mp 177.5-180° C.; 1H NMR (270 MHz, DMSO-d6) 3.80 (3H, s, CH3), 6.50-6.60 (2H, m, ArH), 11.16 (1H, s, OH)

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 h
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-684f4c34193e42d59ba6b0a5c7b2c560
Source dataset
uspto-grants-2014_09
Patent number
US08846737B2

Reaction notes

Loading…