Glyoxylic Acid → 5,7-Bis(1,1-dimethylethyl)-3-(4-methylphenyl)-2(3H)-benzofuranone

HRID 278513Notes

Reaction equation

HRID 278513 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].[C:16]([OH:20])(=O)[CH:17]=O.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:15][C:16](=[O:20])[CH:17]([C:24]3[CH:25]=[CH:26][C:21]([CH3:27])=[CH:22][CH:23]=3)[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 1140TolueneHCID 73112,4-Di-tert-butylphenol

Product 1

HCID 121621655,7-Bis(1,1-dimethylethyl)-3-(4-methylphenyl)-2(3H)-benzofuranoneYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.2 g (0.10 mol) of 2,4-di-tert-butylphenol (97%), 16.3 g (0.11 mol) of 50% aqueous glyoxylic acid, 2.0 g of Fulcat 22B and 50 ml of toluene is refluxed for 8 hours under nitrogen on a water separator. The Fulcat 22B catalyst is then removed by filtration and excess toluene is distilled off on a vacuum rotary evaporator. Crystallisation of the residue from 40 ml of ethanol yields 14.2 g (42%) of 5,7-di-tert-butyl-3-(4-methylphenyl)-3H-benzofuran-2-one, m.p. 130-133° C. (compound (104), Table 1).

Workup

  1. customThe Fulcat 22B catalyst is then removed by filtration and excess toluene
  2. distillationis distilled off on a vacuum rotary evaporator
  3. customCrystallisation of the residue from 40 ml of ethanol

Sources & evidence

ORD record
ord-6f6c258d72d24949852b14b95998962e
Source dataset
uspto-grants-2002_03
Patent number
US06359148B1

Reaction notes

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