Reaktion #65907

Reaktionsgleichung

magnesium

title product

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

Ethylene oxide

→

title compound

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

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe mixture is refluxed for one hour
3. 3
   Temperaturrefluxing
4. 4
   Sonstigepartitioned between saturated ammonium chloride and diethyl ether
5. 5
   ExtraktionThe aqueous layer is further extracted with ether
6. 6
   Waschenthe combined organic extracts washed with brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated

Vorschrift

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.

Quelle