P-Xylene → HCID 10915107, compound

HRID 974725Notes

Reaction equation

HRID 974725 reaction equation
C(O[CH:5]1[C:9]2[CH:10]=[C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=2[O:7][C:6]1=[O:22])(=O)C.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1>O>[C:18]([C:11]1[CH:12]=[C:13]([C:14]([CH3:16])([CH3:17])[CH3:15])[C:8]2[O:7][C:6](=[O:22])[CH:5]([C:29]3[CH:28]=[C:27]([CH3:30])[CH:26]=[CH:25][C:24]=3[CH3:23])[C:9]=2[CH:10]=1)([CH3:20])([CH3:19])[CH3:21]

Participants

4

Reactant 2

HCID 7809P-XyleneHCID 22628567HCID 22628567, compound2×

Product 1

HCID 10915107HCID 10915107, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 15.3 g (50.0 mmol) of 3-acetoxy-5,7-di-tert-butyl-3H-benzofuran-2-one (compound (206), Table 2, Example 2a) in 25 ml (0.20 mol) of p-xylene is added 1.0 g of Fulcat 22B and the mixture is refluxed for 17 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 20 ml of methanol yields 10.5 g (60%) of 5,7-di-tert-butyl-3-(2,5-dimethylphenyl)-3H-benzofuran-2-one, m.p. 93°-97° C. (compound (101), Table 1).

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 20 ml of methanol

Sources & evidence

ORD record
ord-2203fece7ac1450aa7c5cf07cfca8ea3
Source dataset
uspto-grants-1997_03
Patent number
US05607624

Reaction notes

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