反応 #2045057

反応方程式

potassium carbonate

sodium iodide

disodium phosphate

methylchloroacetate

Methylchloroacetate

salicylic acid

triethylamine

→

93

2-Methoxycarbonylmethoxy-benzoic acid methoxycarbonylmethyl ester

溶媒

acetone

acetone

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux for 10 hrs
3. 3
   ろ過Solids were filtered off
4. 4
   温度refluxed for 16 hrs
5. 5
   workup.DISTILLATIONAcetone was distilled off
6. 6
   workup.ADDITIONwater (125 ml) added
7. 7
   抽出Crude 93 was extracted into chloroform
8. 8
   洗浄washed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml)
9. 9
   乾燥dried over sodium sulphate
10. 10
    workup.DISTILLATIONdistilled
11. 11
    その他Crude 93 was purified by column chromatography on silica gel

実験手順

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.

出典