Reaction #2450

Reaction equation

water

9-hydroxymethyl-7, 12-dioxaspiro[5,6]dodecane

p-toluenesulphonic acid

→

9-(2-hydroxyethyl)-7, 11-dioxaspiro[5,5]undecane

Solvents

benzene

Conditions

Workup

1. 1
   OtherThe benzene layer was separated
2. 2
   Extractionthe aqueous layer extracted with benzene
3. 3
   DryingThe combined benzene solution was dried over K2CO3
4. 4
   Otherevaporate to a residue (4 g)

Procedure

A solution of 9-hydroxymethyl-7, 12-dioxaspiro[5,6]dodecane of the formula V (4 g) of the drawings in benzene (15 ml) was stirred at 10° C. for 5 hr with anhydrous p-toluenesulphonic acid (0.2 g). The reaction mixture was made alkaline by adding TEA and water. The benzene layer was separated and the aqueous layer extracted with benzene. The combined benzene solution was dried over K2CO3 and evaporate to a residue (4 g). It was chromatograped on silicagel using chloroform-methanol mixture as eluent to give 9-(2-hydroxyethyl)-7, 11-dioxaspiro[5,5]undecane of formula VI (2.8 g) (70%) of the drawings as colorless viscous liquid.

Source