Reaction #64417

Reaction equation

1-Bromopentane

resorcinol

potassium carbonate

→

3-pentyloxyphenol

Solvents

dimethylformamide

Conditions

Workup

1. 1
   FiltrationThis mixture is filtered through Celite
2. 2
   Concentrationconcentrated under vacuum
3. 3
   Extractionextracted 3 times with ether
4. 4
   WashThe combined extracts are washed with saturated sodium chloride
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum
8. 8
   Otherchromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane

Procedure

A mixture of 24.8 ml of 1-Bromopentane, 66.0 g of resorcinol, and 41.5 g of potassium carbonate is stirred in 400 ml of anhydrous dimethylformamide at 60° C. for 17 hours. This mixture is filtered through Celite and concentrated under vacuum. The residue is taken up in water and extracted 3 times with ether. The combined extracts are washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane:ether to yield 3-pentyloxyphenol as a clear oil.

Source