2-Tert-Butylphenol → 1-tert-Butyl-2-(2,3-epoxypropoxy)benzene

HRID 2163385Notes

Reaction equation

HRID 2163385 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.[OH-].[K+]>C(O)C.O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH:14]1[O:16][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 69232-Tert-ButylphenolHCID 7835EpichlorohydrinHCID 14797Potassium Hydroxide

Product 1

HCID 30162201-tert-Butyl-2-(2,3-epoxypropoxy)benzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 40 parts of o-t-butylphenol, 75 parts of epichlorhydrin, and 40 parts of ethanol boiling under reflux with stirring was added dropwise over 10 minutes a solution of 17.6 parts of potassium hydroxide dissolved in 66 parts of ethanol and the minimum amount of water. The mixture was stirred and refluxed for 105 minutes, cooled, diluted with water, and well extracted with ether, which was then washed with water, dried over magnesium sulphate, and evaporated to an oil. Distillation at 144°/8 mm afforded 43 parts of 3-(2-t-butylphenoxy)-1,2-epoxypropane as a clear oil.

Workup

  1. stirringThe mixture was stirred
  2. temperaturerefluxed for 105 minutes
  3. temperaturecooled
  4. extractionwell extracted with ether, which
  5. washwas then washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to an oil
  8. distillationDistillation at 144°/8 mm

Sources & evidence

ORD record
ord-701aa478b49d419b8727d9e8d7f5eacb
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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