p-Toluenesulfonic acid → 3-[(3,5-Di-tert-butyl-4-hydroxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one

HRID 893342Notes

Reaction equation

HRID 893342 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][C:19]1=[O:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:4][C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:18][C:19]2=[O:27])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 321710Oxindole

Product 1

HCID 541311913-[(3,5-Di-tert-butyl-4-hydroxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-oneYield 43.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (5.28 g; 22.5 mmol), 2-oxindole (3.0 g; 22.5 mmol), and p-toluene sulfonic acid (0.25 g) in toluene (100 ml) is heated under reflux for 18 hours. The reaction mixture is cooled and filtered. The residue is washed with ether and dried @80° C. under vacuum for 18 hours to give 3.4 g (43.2%) of a yellow solid, mp 224°-225° C. (lit. mp 227° C.*).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe residue is washed with ether
  6. customdried @80° C. under vacuum for 18 hours

Sources & evidence

ORD record
ord-66e068d9a7064a4886fff50104eb9fd0
Source dataset
uspto-grants-1992_06
Patent number
US05124347

Reaction notes

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