Reaction #1510

Reaction equation

potassium hydroxide

1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid

benzyl bromide

potassium hydroxide

hydrochloric acid

→

1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid

Yield 92.8%

Solvents

water

ethanol

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureby heating
3. 3
   Temperatureunder reflux at that temperature for 2 hours
4. 4
   Temperatureto cool up to room temperature
5. 5
   FiltrationThe resulting deposited product was filtered
6. 6
   Otherrecrystallized from toluene

Procedure

A mixture of 10.60 g (50 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid, 12.85 g (75 mmol) of benzyl bromide, 6.6 g (100 mmol) of 85% potassium hydroxide, 0.525 g (3.5 mmol) of sodium iodide, 200 ml of ethanol and 25 ml of distilled water was heated under reflux at 100° C. for 12 hours. To this reaction mixture was added 50 ml of 10% potassium hydroxide, followed by heating under reflux at that temperature for 2 hours. After allowing the reaction system to cool up to room temperature, the reaction mixture in cold water was acidified with 36% hydrochloric acid. The resulting deposited product was filtered, and recrystallized from toluene to obtain 13.08 g (46.4 mmol) of 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid.

Source