2,4-Di-tert-butylphenol → 5,7-Di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one

HRID 375991Notes

Reaction equation

HRID 375991 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].O.[OH:17][C:18]1[CH:28]=[CH:27][C:21]([CH:22](O)[C:23](O)=[O:24])=[CH:20][CH:19]=1>C(O)(=O)C>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:15][C:23](=[O:24])[CH:22]([C:21]3[CH:27]=[CH:28][C:18]([OH:17])=[CH:19][CH:20]=3)[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 126772902-Hydroxy-2-(4-hydroxyphenyl)acetic acid hydrate

Product 1

HCID 189914135,7-Di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-oneYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 103.2 g (0.50 mol) of 2,4-di-tert-butylphenol and 102.4 g (0.55 mol) of 4-hydroxymandelic acid monohydrate in 100 ml of acetic acid is refluxed for 24 hours under a nitrogen atmosphere. The reaction mixture is then diluted with 140 ml of 50% aqueous acetic acid, cooled, and the precipitate formed is filtered off. The residue is washed with another 200 ml of 50% aqueous acetic acid and then dried, giving 95.9 g (57%) of 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one, melting point 187°-190° C. (compound (101), Table 1).

Workup

  1. temperatureis refluxed for 24 hours under a nitrogen atmosphere
  2. temperaturecooled
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washThe residue is washed with another 200 ml of 50% aqueous acetic acid
  6. customdried

Sources & evidence

ORD record
ord-93924a4670c44f8392802fc2e052d050
Source dataset
uspto-grants-1996_01
Patent number
US05488117

Reaction notes

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