Reaction #170975

Reaction equation

methyl 6-bromohexanoate

4-nitrophenol

potassium carbonate

sodium iodide

→

21

Yield 65.2%

6-(4-Nitrophenoxy)-hexanoic acid methyl ester

Yield 65.2%

Solvents

acetone

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   Temperatureto reflux for 48 hours
3. 3
   workup.DISTILLATIONAcetone was distilled off
4. 4
   workup.ADDITIONwater (2 L) was added
5. 5
   FiltrationCrude 21 was filtered
6. 6
   Otherdried
7. 7
   Otherrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Procedure

To a mixture of 4-nitrophenol (150 g, 1.079 moles), potassium carbonate (600 g, 4.341 moles) and sodium iodide (10 g, 66.7 mmol) in anhydrous acetone (2.1 L) was added methyl 6-bromohexanoate (156 g, 746.41 mmol) with and heating to reflux for 48 hours. Acetone was distilled off and water (2 L) was added. Crude 21 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 21 (130 g, 45.1%) as a white powder with an m.p. between 84.5.5-86.6° C.

Source