Dimethylamine → Phenol, 2,6-bis(1,1-dimethylethyl)-4-(2-methyl-1-propenyl)-

HRID 544752Notes

Reaction equation

HRID 544752 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH:16](=O)[CH:17]([CH3:19])[CH3:18].CNC>C(O)(C)C>[CH3:18][C:17]([CH3:19])=[CH:16][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6561IsobutyraldehydeHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 13548084Phenol, 2,6-bis(1,1-dimethylethyl)-4-(2-methyl-1-propenyl)-Yield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,6-di-tertiary-butyl phenol (4.1 g; 20 mmol), isobutyraldehyde (3 ml; 33 mmol), dimethylamine (1.5 g; 34 mmol) dissolved in isopropanol (7.5 g) were charged to a 100 ml glass vessel and refluxed at ambient pressure under nitrogen for 48 hours. The resultant reaction mixture was allowed to cool to ambient temperature and concentrated to a yellow oil which was recrystallized from a mixture of ethanol and water (90:10) to give yellow crystals (3.7 g; 71% yield) of 1,1-dimethyl-2-(3',5'-di-t-butyl-4'-hydroxyphenyl)ethene as characterized by VPC, mass spectroscopy and NMR.

Workup

  1. additionwere charged to a 100 ml glass vessel
  2. temperaturerefluxed at ambient pressure under nitrogen for 48 hours
  3. customThe resultant reaction mixture
  4. concentrationconcentrated to a yellow oil which
  5. customwas recrystallized from a mixture of ethanol and water (90:10)

Sources & evidence

ORD record
ord-b33af0ba02da41a2aae39a57a46d0a2a
Source dataset
uspto-grants-1984_05
Patent number
US04451676

Reaction notes

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