I've been wondering how easy was the methylation reaction of salicylic acid?
No, not the esterification of the carboxyl group but the ether formation of the hydroxyl (to yield o-anisic acid in the end).
I could find dozens of descriptions and lab manuals where the synthesis of the "oil of wintergreen" was described but not the other.
Am I doing something wrong or do I overlook something obvious why the o-anisic acid synth could not be performed the way I want it?
Is it a bit more complicated than "dissolve the salicylic acid in some excess NaOH solution, stirr vigorously, add some dimethyl-sulfate in excess,
stirr for a while, get rid of unreacted methylating agent, enjoy your o-anisic acid"? dawt - 24-5-2020 at 11:34
Is it a bit more complicated than "dissolve the salicylic acid in some excess NaOH solution, stirr vigorously, add some dimethyl-sulfate in excess,
stirr for a while, get rid of unreacted methylating agent, enjoy your o-anisic acid"?
Salicylic acid 200 g and potassium carbonate 415.6 g were charged in Acetone 1000 mL and Dimethyl sulfate 403 g was added slowly at 25-30°C. The
reaction was maintained at 55-60°C for 3-4 hrs and reaction progress was monitored by TLC. The reaction mixture was cooled to 25-30°C and filtered
remove salts. The resulting filtrate concentrated under vacuum to obtained 2-Methoxy-benzoic acid methyl ester.
Saponificate that and you end up with your target compound.
