Reaction #725879

Reaction equation

methyl salicylate

K2CO3

methyl chloroacetate

→

1

Yield 17.0%

2-Methoxycarbonylmethoxy-benzoic acid methyl ester

Yield 17.0%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 36 hours
2. 2
   workup.DISTILLATIONThe acetone was distilled off
3. 3
   workup.ADDITIONwater (1200 ml) was added
4. 4
   ExtractionCrude 1 was extracted into chloroform
5. 5
   Dryingdried over Na2SO4
6. 6
   workup.DISTILLATIONdistilled
7. 7
   Otherpurified by column chromatography on silica gel

Procedure

To a mixture of methyl salicylate (100 g, 657 mmol) and anhydrous K2CO3 (360 g, 2.605 mol) in anhydrous acetone (1000 ml) was added methyl chloroacetate (94 g, 866 mmol) and refluxed for 36 hours. The acetone was distilled off and water (1200 ml) was added. Crude 1 was extracted into chloroform, dried over Na2SO4 distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 1 (25 grams, 17%) as a light yellow syrup.

Source