Reaction #2044995

Reaction equation

methyl chloroacetate

methyl 2,5-dihydroxybenzoate

K2CO3

sodium iodide

acetone

→

4

Yield 80.0%

2,5-Bismethoxycarbonylmethoxybenzoic acid methyl ester

Yield 80.0%

Conditions

Workup

1. 1
   Temperaturerefluxed 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
   Otherdried
6. 6
   Otherrecrystallised from toluene

Procedure

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