Reaction #64418

Reaction equation

3-pentyloxyphenol

NaH

3-Bromopropanol

→

3-[3-(pentyloxy)phenoxy]propanol

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   Temperatureis cooled in an ice bath
2. 2
   OtherThe solvent is removed under vacuum
3. 3
   OtherThe residue obtained
4. 4
   Otherchromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane

Procedure

A mixture of 0.80 g of 60% NaH in 28 ml of anhydrous dimethylformamide is cooled in an ice bath. To this is added 3.01 g of the above 3-pentyloxyphenol oil dissolved in 7 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 1.81 ml of 3-Bromopropanol are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum, and the residue worked up in same manner as above. The residue obtained is flash chromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane:ether to yield 3-[3-(pentyloxy)phenoxy]propanol as a pale yellow oil.

Source