Reacción #2045027

Ecuación de reacción

methyl 6-bromohexanoate

4-nitrophenol

potassium carbonate

sodium iodide

→

39

Rendimiento 65.2%

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

Rendimiento 65.2%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 48 hours
3. 3
   workup.DISTILLATIONAcetone was distilled off
4. 4
   workup.ADDITIONwater (2 L) was added
5. 5
   FiltraciónCrude 39 was filtered
6. 6
   Otrodried
7. 7
   Otrorecrystallised from a mixture of ethyl acetate:hexane (1:6)

Procedimiento

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) and heated to reflux for 48 hours. Acetone was distilled off and water (2 L) was added. Crude 39 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 39 (130 g, 45.1%) as a white powder. M.p: 84.5.5-86.6° C.

Fuente