P-Xylene → HCID 10915107, compound

HRID 2395421Notes

Reaction equation

HRID 2395421 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][C:24]([CH3:27])=[CH:25][CH:26]=1>O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:17])[CH3:18])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:26]3[CH:25]=[C:24]([CH3:27])[CH:23]=[CH:22][C:21]=3[CH3:20])[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7809P-XyleneHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone2×

Product 1

HCID 10915107HCID 10915107, compoundYield 80.1%

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 p-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 rotaray evaporator. Crystallisation of the residue from 400 ml of methanol yields 280.6 g (80%) 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 rotaray evaporator
  3. customCrystallisation of the residue from 400 ml of methanol

Sources & evidence

ORD record
ord-8a5bf6bb366848b6ae35ce4fa4c08044
Source dataset
uspto-grants-1998_09
Patent number
US05814692

Reaction notes

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