Reaction #56591

Reaction equation

sodium bicarbonate

ether

dihydropyrane

6-chlorohexanol

→

product

Yield 86.6%

2-(6-Chlorohexyloxy)tetrahydropyrane

Yield 86.6%

Solvents

methylenechloride

methylenechloride

Conditions

Workup

1. 1
   WashThe ether phase was washed with water
2. 2
   Dryingdried over sodium sulphate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated to dryness

Procedure

To a mixture of 15 g of 6-chlorohexanol, 100 ml of methylenechloride and 0.2 g of p-toluenesulphonic acid were added dropwise 12 g of dihydropyrane in 40 ml of methylenechloride. The reaction mixture was stirred for 15 h at room temperature and then distributed between ether and saturated sodium bicarbonate solution. The ether phase was washed with water, dried over sodium sulphate, filtered and concentrated to dryness. Chromatography of the residue on silica using hexane/ether (3:1) gave 21 g of the product as a colourless oil.

Source