تفاعل #65907

معادلة التفاعل

magnesium

title product

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

Ethylene oxide

→

title compound

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

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   درجة الحرارةthe mixture is refluxed for one hour
3. 3
   درجة الحرارةrefluxing
4. 4
   أخرىpartitioned between saturated ammonium chloride and diethyl ether
5. 5
   استخلاصThe aqueous layer is further extracted with ether
6. 6
   غسيلthe combined organic extracts washed with brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated

الإجراء التجريبي

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.

المصدر