Reaction #56590

Reaction equation

2-(6-chlorohexyloxy)tetrahydropyrane

hydroquinone

potassiumcarbonate

potassiumiodide

→

product

Yield 82.5%

4-(6-(2-Tetrahydropyranyl)oxyhexyloxy)phenol

Yield 82.5%

Solvents

dimethylsulfoxide

water

Conditions

Workup

1. 1
   Otherto react for 4 days at 80° C
2. 2
   Extractionextracted with ether
3. 3
   DryingThe organic phase was then dried over sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated to dryness

Procedure

A mixture of 10 g of 2-(6-chlorohexyloxy)tetrahydropyrane, 25 g of hydroquinone, 31 g of potassiumcarbonate, 0.752 g of potassiumiodide and 250 ml of dimethylsulfoxide was allowed to react for 4 days at 80° C. Subsequently, the reaction mixture was cooled to room temperature and after addition of water extracted with ether. The organic phase was then dried over sodium sulphate, filtered and concentrated to dryness. Chromatography on silica with 10% ethylacetate in toluene gave 11 g of product as a yellowish oil.

Source