Reaction #1308

Reaction equation

5-(3-bromophenyl)-2-methyl-pentan-2-ol

Compound E

5-(3-bromophenyl)-2-methyl-pentan-2-ol

H2SO4

→

title compound

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

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with Et2O (3×40 ml)
2. 2
   WashThe combined organic layers were washed with water, sat. aqueous NaHCO3 and brine
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherPurification
6. 6
   workup.DISTILLATIONby kugelrohr distillation

Procedure

15.0 g (58.3 mmol) of 5-(3-bromophenyl)-2-methyl-pentan-2-ol (Compound E) was cooled to 0° C. and then 2.8 ml of conc. H2SO4 was added. The mixture was stirred for 2.5 hours, diluted with water (20 ml) and extracted with Et2O (3×40 ml). The combined organic layers were washed with water, sat. aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Purification by kugelrohr distillation gave the title compound as a colorless oil.

Source