Methanol → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Reaction equation

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

Participants

Reactant 3

HCID 887Methanol

HCID 94475-Chlorosalicylic Acid

HCID 24386Thionyl Chloride

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Procedure

To a cold solution of 100 ml methanol is slowly added 100 ml thionyl chloride followed by 30 g of 5-chlorosalicylic acid. This is then refluxed overnight, the solvent removed and the residue dissolved in ether. The ether is washed with a sodium bicarbonate solution, water, dried over magnesium sulfate and evaporated to dryness to obtain methyl 5-chlorosalicylate which is used directly in the next step.