Reaction #65907

Reaction equation

magnesium

title product

2,4-bis(1,1-dimethylethyl)-1-bromobenzene

Ethylene oxide

→

title compound

2,4-bis(1,1-dimethylethyl)benzeneethanol

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturethe mixture is refluxed for one hour
3. 3
   Temperaturerefluxing
4. 4
   Otherpartitioned between saturated ammonium chloride and diethyl ether
5. 5
   ExtractionThe aqueous layer is further extracted with ether
6. 6
   Washthe combined organic extracts washed with brine
7. 7
   Dryingdried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated

Procedure

To 243 mg (10 mmoles) of magnesium turnings in 10 ml of tetrahydrofuran is added dropwise a solution of 2.69 grams (10 mmoles) of the title product of Example 9 in 5 ml of tetrahydrofuran. After the addition is complete, the mixture is refluxed for one hour. Ethylene oxide (440 mg, 10 mmoles) is then added, and refluxing continued for one hour. The mixture is cooled to room temperature and partitioned between saturated ammonium chloride and diethyl ether. The aqueous layer is further extracted with ether, the combined organic extracts washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Source