Diisopropyl Ether → 2,4-Di-tert-butyl-6-(prop-2-en-1-yl)phenol

HRID 1030449Notes

Reaction equation

HRID 1030449 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15]CC=C)([CH3:4])([CH3:3])[CH3:2].[CH:19](OC(C)C)([CH3:21])[CH3:20]>>[CH2:21]([C:7]1[CH:8]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]=1[OH:15])[CH:19]=[CH2:20]

Participants

3

Reactant 2

HCID 7914Diisopropyl EtherHCID 50888872HCID 50888872, compound

Product 1

HCID 151106652,4-Di-tert-butyl-6-(prop-2-en-1-yl)phenol

Procedure

10 g of 2,4-di-tert-butylallyloxybenzene are heated under nitrogen to 245° C. for 45 minutes. The yellow crude oil is taken up in diisopropyl ether. The ether phase is washed with 3 % sodium hydroxide and then with water. After drying and evaporation of the solvent, the oil obtained (7.6 g) is chromatographed on silica gel 60 (eluent: 80/20 heptane/CH2Cl2). A pale-yellow oil of 2-allyl-4,6-di-tert-butylphenol is obtained (5.4 g, yield =54 %).

Workup

  1. washThe ether phase is washed with 3 % sodium hydroxide
  2. customAfter drying
  3. customevaporation of the solvent
  4. customthe oil obtained (7.6 g)
  5. customis chromatographed on silica gel 60 (eluent: 80/20 heptane/CH2Cl2)

Sources & evidence

ORD record
ord-d6fe5a38dc184a6690aa0d092ba36b39
Source dataset
uspto-grants-1992_04
Patent number
US05106611

Reaction notes

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