Réaction #725880

Équation de réaction

methyl chloroacetate

methyl 2,5-dihydroxybenzoate

K2CO3

sodium iodide

acetone

→

4

Rendement 80.0%

2,5-Bismethoxycarbonylmethoxybenzoic acid methyl ester

Rendement 80.0%

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 20 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) was added
4. 4
   FiltrationCrude 4 was filtered
5. 5
   Autredried
6. 6
   Autrerecrystallised from toluene

Mode opératoire

To a mixture of methyl 2,5-dihydroxybenzoate (34 g, 202 mmol), anhydrous K2CO3 (204 g, 1.476 mol) and sodium iodide (5 grams, 33.3 mmol) in anhydrous acetone (1000 ml) was added methyl chloroacetate (60.7 grams, 559 mmol) and refluxed for 20 hours. Acetone was distilled off and water (1500 ml) was added. Crude 4 was filtered, dried and recrystallised from toluene to give pure 4 (50.5 g, 80%) as a cream colored powder. The melting point was found to be 90-94° C. The structure was confirmed by NMR.

Source