Reaction #2045057

Reaction equation

potassium carbonate

sodium iodide

disodium phosphate

methylchloroacetate

Methylchloroacetate

salicylic acid

triethylamine

→

93

2-Methoxycarbonylmethoxy-benzoic acid methoxycarbonylmethyl ester

Solvents

acetone

acetone

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 10 hrs
3. 3
   FiltrationSolids were filtered off
4. 4
   Temperaturerefluxed for 16 hrs
5. 5
   workup.DISTILLATIONAcetone was distilled off
6. 6
   workup.ADDITIONwater (125 ml) added
7. 7
   ExtractionCrude 93 was extracted into chloroform
8. 8
   Washwashed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml)
9. 9
   Dryingdried over sodium sulphate
10. 10
    workup.DISTILLATIONdistilled
11. 11
    OtherCrude 93 was purified by column chromatography on silica gel

Procedure

Methylchloroacetate (9.4 g, 86.66 mmol) was added dropwise to a mixture of salicylic acid (10 g, 72.46 mmol) and triethylamine (8.8 g, 86.96 mmol) in acetone (50 ml) and heated to reflux for 10 hrs. Solids were filtered off and potassium carbonate (25 g, 180.89 mmol) was added to the acetone layer together with sodium iodide (2 gm, 13.34 mmol), disodium phosphate (2 g, 14.16 mmol) and methylchloroacetate (9.4 g, 86.66 mmol) and refluxed for 16 hrs. Acetone was distilled off and water (125 ml) added. Crude 93 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml), dried over sodium sulphate and distilled. Crude 93 was purified by column chromatography on silica gel using benzene to get pure 93 (12 g, 58.7%) as a syrup.

Source