4-tert-Butylphenol → 4-tert-Butylphenyl glycidyl ether, (+)-

HRID 237729Notes

Reaction equation

HRID 237729 reaction equation
[CH2:1]([C@@H:3]1[O:5][CH2:4]1)Cl.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:1][C@@H:3]2[CH2:4][O:5]2)=[CH:14][CH:15]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-Yield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of (R)-epichlorohydrin (12.4 g, 134 mmol) and 4-tert-butylphenol (10.0 g, 66.8 mmol) in acetone (50 ml) was added potassium carbonate (9.24 g, 66.8 mmol). The mixture was stirred at 45° C. for 96 hours. The reaction mixture was then concentrated to remove acetone. The residue was partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic phases were combined and washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by flash chromatography (silica, methylene chloride/heptane) to give 9.18 g (67%) of (S)-2-(4-tert-butyl-phenoxymethyl)oxirane.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove acetone
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue was purified by flash chromatography (silica, methylene chloride/heptane)

Sources & evidence

ORD record
ord-513245e328264cf5b9f40f2df61fdfd0
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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