반응 #2045057

반응 방정식

potassium carbonate

sodium iodide

disodium phosphate

methylchloroacetate

Methylchloroacetate

salicylic acid

triethylamine

→

93

2-Methoxycarbonylmethoxy-benzoic acid methoxycarbonylmethyl ester

용매

acetone

acetone

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 10 hrs
3. 3
   여과Solids were filtered off
4. 4
   온도refluxed for 16 hrs
5. 5
   workup.DISTILLATIONAcetone was distilled off
6. 6
   workup.ADDITIONwater (125 ml) added
7. 7
   추출Crude 93 was extracted into chloroform
8. 8
   세척washed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml)
9. 9
   건조dried over sodium sulphate
10. 10
    workup.DISTILLATIONdistilled
11. 11
    기타Crude 93 was purified by column chromatography on silica gel

실험 절차

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.

출처