O-Xylene → 2(3H)-Benzofuranone

HRID 618876Notes

Reaction equation

HRID 618876 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[CH3:27]>O>[O:12]1[C:8]2[CH:7]=[CH:6][CH:5]=[CH:15][C:9]=2[CH2:10][C:11]1=[O:13].[CH3:20][C:21]1[CH:22]=[C:23]([CH:10]2[C:9]3[CH:15]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:8]=3[O:12][C:11]2=[O:13])[CH:24]=[CH:25][C:26]=1[CH3:27]

Participants

5

Reactant 2

HCID 7237O-XyleneHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone2×

Product 2

HCID 683822(3H)-BenzofuranoneHCID 99503072(3H)-Benzofuranone, 5,7-bis(1,1-dimethylethyl)-3-(3,4-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 262.3 g (1.00 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example 1a) in 500 ml (4.05 mol) of o-xylene are added 40 g of Fulcat 22B and the mixture is refluxed for 1.5 hours on a water separator. The Fulcat 22B catalyst is then removed by filtration and excess p-xylene is removed by distillation on a vacuum rotary evaporator. Crystallisation of the residue from 500 ml of methanol yields 244 g (69%) of 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl)-3H-benzofuran-2-one, m.p. 130-132° C. (compound (103), Table 1), which additionally contains c. 1.3% of the structural isomer [3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-3H-benzofuran-2-one, compound (103A)]. The mother liquor yields a further 42.4 g of product which, according to GC-MS analysis, consists of 12.3% of the compound (103) and 87.7% of the isomeric compound (103A).

Workup

  1. customThe Fulcat 22B catalyst is then removed by filtration and excess p-xylene
  2. customis removed by distillation on a vacuum rotary evaporator
  3. customCrystallisation of the residue from 500 ml of methanol

Sources & evidence

ORD record
ord-cc2e4364c2fa4663be9cec61d65bfd0a
Source dataset
uspto-grants-1999_09
Patent number
US05955619

Reaction notes

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