Reaction #1311

Reaction equation

4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Compound I

4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

cyclohexanol

sodium

sodium

cyclohexanol

→

title compound

6-Bromo-4-cyclohexyloxy-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene

Conditions

Workup

1. 1
   Temperaturewas cooled to ambient temperature
2. 2
   TemperatureThe mixture was heated at 120° C. for 4 hours
3. 3
   workup.DISTILLATIONthe excess solvent distilled off under reduced pressure
4. 4
   workup.DISSOLUTIONThe product was dissolved in Et2O (75 ml)
5. 5
   Washwashed with water (5 ml) and brine (5 ml)
6. 6
   Dryingdried over MgSO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherPurification by column chromatography (silica, 5% EtOAc-hexane)

Procedure

To 9 g (89.9 mmol) of cyclohexanol was added 160 mg (7.0 mmol) of sodium metal and the mixture was stirred at 70° C. for 12 hours. After all of the sodium dissolved the reaction mixture was cooled to ambient temperature and then a solution of 1 g (3.2 mmol) of 4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound I) in 1 ml of cyclohexanol was added. The mixture was heated at 120° C. for 4 hours and thereafter the excess solvent distilled off under reduced pressure. The product was dissolved in Et2O (75 ml), washed with water (5 ml) and brine (5 ml), dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (silica, 5% EtOAc-hexane) yielded the title compound as a colorless oil.

Source