Reaktion #54365

Reaktionsgleichung

3-(3-benzyloxyphenyl)butyl tosylate

phenol

sodium hydride

→

product

3-(3-Benzyloxyphenyl)-1-phenoxybutane

Lösungsmittel

dimethylformamide

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenpreviously washed with pentane) in dimethylformamide (70 ml.) at 60° C
2. 2
   workup.STIRRINGThe reaction mixture is stirred at 80° C. for a half hour
3. 3
   Extraktionextracted with ether (4 × 400 ml.)
4. 4
   WaschenThe combined extracts are washed successively with cold 2N hydrochloric acid (2 × 300 ml.) and saturated sodium chloride solution (3 × 300 ml.)
5. 5
   Trocknendried (Na2SO4)
6. 6
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

A solution of phenol (4.56 g., 48.6 mmole) in dimethylformamide (40 ml.) is added under a nitrogen atmosphere to a suspension of sodium hydride (2.32 g., 48.6 mmole) of 50% previously washed with pentane) in dimethylformamide (70 ml.) at 60° C. The reaction mixture is stirred for one hour at 60°-70° C., after which a solution of 3-(3-benzyloxyphenyl)butyl tosylate (18.9 g., 46 mmole) in dimethylformamide (80 ml.) is added. The reaction mixture is stirred at 80° C. for a half hour and is then cooled to room temperature, diluted with cold water (2500 ml.) and extracted with ether (4 × 400 ml.). The combined extracts are washed successively with cold 2N hydrochloric acid (2 × 300 ml.) and saturated sodium chloride solution (3 × 300 ml.) and then dried (Na2SO4). Removal of the solvent under reduced pressure affords the product as an oil. The oily residue is dissolved in benzene and filtered through silica gel (100 g.). Concentration of the filtrate under reduced pressure gives the product as an oil.

Quelle