Reaction #6610

Reaction equation

water

4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

potassium carbonate

iodoethane

→

title compound

Yield 40.9%

4-Carbethoxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

Yield 40.9%

Solvents

butanone

Conditions

Workup

1. 1
   Extractionextracted with ether
2. 2
   Washthe organic phase was washed with water
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   OtherRecrystallization from methanol

Procedure

2 g (6 mmol) of 4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether, 2.7 g (19.6 mmol) of anhydrous potassium carbonate and 19 g (12.4 mmol) of iodoethane in 18 ml of butanone were refluxed for 7 h. The mixture was then poured into water and extracted with ether, and the organic phase was washed with water, dried over Na2SO4 and concentrated. Recrystallization from methanol resulted in 0.9 g of the title compound of melting point 76°-77° C.

Source