Reaction #6608

Reaction equation

sodium sulfate

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

lithium aluminum hydride

water

→

4-Aminomethylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetra-methyl-2-naphthyl ether

Solvents

ether

ether

Conditions

Workup

1. 1
   Temperatureunder reflux for 3 h
2. 2
   Temperaturecooled
3. 3
   ExtractionThe mixture was extracted three times with ether
4. 4
   Washthe combined ether extracts were washed with water
5. 5
   Dryingdried over Na2SO4
6. 6
   Concentrationconcentrated

Procedure

A suspension of 3 g (9.4 mmol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether in 60 ml of ether was added dropwise under nitrogen to a suspension of 1 g (26 mmol) of lithium aluminum hydride in 50 ml of dry ether at 25° C. The mixture was then stirred under reflux for 3 h, cooled and hydrolyzed cautiously with water and sodium sulfate solution. The mixture was extracted three times with ether, and the combined ether extracts were washed with water, dried over Na2SO4 and concentrated. 3 g of the title compound of melting point 77°-79° C. remained.

Source