N,N-Dimethylaniline → 4-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenol

HRID 1900502Notes

Reaction equation

HRID 1900502 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].CN(C)[C:25]1[CH:30]=CC=C[CH:26]=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]([CH2:30][CH:25]=[CH2:26])[C:6]=1[C:19]([CH3:22])([CH3:20])[CH3:21])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 110880374-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

Product 1

HCID 111202654-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenolYield 77%

Procedure

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-(2-propenyl)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-1abf54f94df443168d367ca6339e3383
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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