Methanol → 2-Chloro-4-hydroxy-benzoic acid methyl ester

HRID 1166714Notes

Reaction equation

HRID 1166714 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Procedure

To a solution 2-chloro-4-hydroxybenzoic acid in anhydrous methanol was added thionyl chloride (1.5 eq). After stirring the solution at room temperature for 16 hours, the solvent was evaporated. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate, water, brine, and dried over MgSO4 and concentrated in vacuo to give methyl 2-chloro-4-hydroxybenzoate.

Workup

  1. customthe solvent was evaporated
  2. washwashed with saturated aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f3463cb30f7453193e4f91e0da6a00a
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

Loading…