2,4-Di-tert-butylphenol → 3-(4-Allyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one

HRID 22574

Reaction equation

HRID 22574 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[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:19][C:20]1[CH:30]=[CH:29][C:23]([CH:24](O)[C:25](O)=[O:26])=[CH:22][CH:21]=1)[CH:17]=[CH2:18]>>[CH2:16]([O:19][C:20]1[CH:30]=[CH:29][C:23]([CH:24]2[C:7]3[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=3[O:15][C:25]2=[O:26])=[CH:22][CH:21]=1)[CH:17]=[CH2:18]

Participants

3

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 199305644-Allyloxymandelic acid

Product 1

HCID 199305653-(4-Allyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-oneYield 61%

Procedure

A mixture of 309 g (1.50 mol) of 2,4-di-tert-butyl-phenol and 192 g (1.00 mol) of 4-allyloxymandelic acid (prepared in accordance with EP-B-182 507, Example 1, page 4) is stirred under nitrogen for 2 hours at 140°-150° C. Then the mixture is stirred under low vacuum (50 mbar) for 1.5 hours; at 150° C. Excess 2,4-di-tert-butylphenol is distilled off under a high vacuum. Crystallisation of the residue from xylene and ethanol gives 230.1 g (61% ) of 3-(4-allyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one of m.p. 112°-114° C.

Workup

  1. stirringThen the mixture is stirred under low vacuum (50 mbar) for 1.5 hours
  2. customat 150° C
  3. distillationExcess 2,4-di-tert-butylphenol is distilled off under a high vacuum
  4. customCrystallisation of the residue from xylene and ethanol

Sources & evidence

ORD record
ord-444aa798566c4ee8a5054b05e0eaa311
Source dataset
uspto-grants-1995_06
Patent number
US05428177

Linked notes

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