Ethylene Oxide → 2,4-Bis(1,1-dimethylethyl)benzeneethanol

HRID 37629Notes

Reaction equation

HRID 37629 reaction equation
[Mg].[CH3:2][C:3]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1Br)([CH3:5])[CH3:4].[CH2:17]1[O:19][CH2:18]1>O1CCCC1>[CH3:2][C:3]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[CH2:17][CH2:18][OH:19])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 5462224MagnesiumHCID 110764641-Bromo-2,4-di-tert-butylbenzene

Product 1

HCID 199360802,4-Bis(1,1-dimethylethyl)benzeneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed for one hour
  3. temperaturerefluxing
  4. custompartitioned between saturated ammonium chloride and diethyl ether
  5. extractionThe aqueous layer is further extracted with ether
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4db0bebb53404ac29f05848985b87693
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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