Reaction #2045009

Reaction equation

methyl 6-bromohexanoate

Paracetamol

K2CO3

sodium iodide

→

19

Yield 66.0%

6-(4-Acetylamino-phenoxy)-hexanoic acid methyl ester

Yield 66.0%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 60 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (3 liter) was added
4. 4
   FiltrationCrude 19 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from a mixture of chloroform:hexane (1:5)

Procedure

To a mixture of Paracetamol (250 g, 1.654 mol), anhydrous K2CO3 (800 g, 5.789 mol) and sodium iodide (17 g, 113 mmol) in anhydrous acetone (5 liters) was added methyl 6-bromohexanoate (470 g, 2.25 mol) and refluxed for 60 hours. Acetone was distilled off and water (3 liter) was added. Crude 19 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 19 (195 g, 66%) as a white powder. The melting point was found to be 96.4-98.8° C. The product was tested by HPLC and found to be 99%+ pure. The structure was confirmed with NMR.

Source