Reaction #2045001

Reaction equation

methyl 2-chloropropionate

Capsaicin

K2CO3

sodium iodide

→

11

Yield 31.2%

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

Yield 31.2%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 16 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   FiltrationCrude 11 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from a mixture of chloroform:hexane (1:5)

Procedure

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), and sodium iodide (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 2-chloropropionate (1.2 g, 10 mmol) and refluxed for 16 hours. Acetone was distilled off and water (15 ml) was added. Crude 11 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 11 (0.8 g, 31.2%) as a white powder. The melting point was found to be 62.3-64° C.

Source