Allyl bromide → 4-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

HRID 1900501Notes

Reaction equation

HRID 1900501 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH:28]=[CH2:29]>CC(C)=O>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:9][C:8]([O:15][CH2:29][CH:28]=[CH2:27])=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

Product 1

HCID 110880374-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Acetoxy-3,5-di-tert-butylphenol (10 g) and potassium carbonate (15.6 g) were dissolved in acetone (300 ml). After addition of 3-bromo-1-propene (6.55 ml), the mixture was refluxed for 24 h. The reaction mixture was concentrated under reduced pressure and water was added to the concentrate. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene (11 g) as a colorless liquid in a quantitative yield.

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added to the concentrate
  4. extractionThe mixture was subjected to extraction with diethyl ether
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-c55cf6fda1854716848258c3fdd0ef37
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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