Reaction #2045000

Reaction equation

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl chloroacetate

→

10

Yield 71.4%

{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

Yield 71.4%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 6 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (150 ml) was added
4. 4
   FiltrationCrude 10 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from toluene

Procedure

To a mixture of Capsaicin (17 g, 55.7 mmol), anhydrous K2CO3 (26 g, 188 mmol), sodium iodide (4.5 g, 30 mmol) and disodium phosphate (4.5 g, 32 mmol) in anhydrous acetone (425 ml) was added methyl chloroacetate (9 g, 83 mmol) and refluxed for 6 hours. Acetone was distilled off and water (150 ml) was added. Crude 10 was filtered, dried and recrystallised from toluene to give pure 10 (15 g, 71.4%) as a white power. The melting point was found to be 99.5-103.5° C. It was analyzed by HPLC and found to be 99.3% pure.

Source