4-Acetoxy-3,5-Di-tert-Butyl-2-(2-Propenyloxy)phenol 4-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene → 4-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenol

HRID 1452359Notes

Reaction equation

HRID 1452359 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15]CC=C)=[CH:7][C:6]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:3])[CH3:2].C(O[C:27]1[C:32](C(C)(C)C)=CC(O)=C(OCC=C)[C:28]=1C(C)(C)C)(=O)C>CN(C)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:9][C:8]([OH:15])=[C:7]([CH2:32][CH:27]=[CH2:28])[C:6]=1[C:19]([CH3:22])([CH3:20])[CH3:21])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 199736404-Acetoxy-3,5-Di-tert-Butyl-2-(2-Propenyloxy)phenol 4-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

Product 1

HCID 111202654-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenolYield 165%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Procedure

Synthesis of 4-Acetoxy-3,5-Di-tert-Butyl-2-(2-Propenyloxy)phenol 4-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene (11.0 g) was dissolved in N,N-dimethylaniline (50 ml) and the solution was refluxed for 18 h under a nitrogen atmosphere. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and purified by silica gel chromatography (15% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-2-(2propenyl)phenol [8.84 g (yield, 77%)] as a white solid.

Workup

  1. temperaturethe solution was refluxed for 18 h under a nitrogen atmosphere
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. custompurified by silica gel chromatography (15% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-6fea902826dd4b1f8b295fcb35e02394
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

Loading…