Reaktion #727273

Reaktionsgleichung

1-bromobutane

4-bromobenzyl alcohol

sodium hydride

→

title compound

Ausbeute 89.0%

1-Bromo-4-butoxymethyl-benzene

Ausbeute 89.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C
2. 2
   workup.STIRRINGThis mixture was stirred for 40 minutes at room temperature
3. 3
   workup.STIRRINGstirred for 25 minutes at 70° C
4. 4
   SonstigeThe reaction solution was partitioned into water and ethyl acetate at 0° C
5. 5
   WaschenThe organic layer was washed with water and saturated aqueous sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was evaporated under a reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1)

Vorschrift

To a solution of 4-bromobenzyl alcohol (10.0 g, 53.5 mmol) in N,N-dimethylformamide (200 mL) was added sodium hydride (3.08 g, 64.2 mmol, 50% in oil) at 0° C. This mixture was stirred for 5 minutes at 0° C., and 1-bromobutane (7.47 mL, 69.3 mmol) was added thereto at 0° C. This mixture was stirred for 40 minutes at room temperature and then stirred for 25 minutes at 70° C. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the title compound (11.5 g, 89%).

Quelle