Phenol → 3,3-bis(4-hydroxyphenyl)-7-methyl-1,3-dihydro-2H-indol-2-one

HRID 972544Notes

Reaction equation

HRID 972544 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[C:14]2=O.[C:20]1([O:26]C(C)=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O.S(=O)(=O)(O)O>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:14]2([C:23]3[CH:24]=[CH:25][C:20]([OH:26])=[CH:21][CH:22]=3)[C:13]3[C:17](=[C:9]([CH3:8])[CH:10]=[CH:11][CH:12]=3)[NH:16][C:15]2=[O:18])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 143137-MethylisatinHCID 31229Phenyl acetate

Product 1

HCID 38606403,3-bis(4-hydroxyphenyl)-7-methyl-1,3-dihydro-2H-indol-2-oneYield 58.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

38.2 g of pure phenol were mixed with 0.4 g of concentrated sulphuric acid, with stirring and heating to 60° C. 28.5 g (0.177 mole) of 7-methylisatin were added in portions. At the end of the addition, the temperature was raised to 85° C. and 21 g of PhOAc were gradually added dropwise over a period of 5 hours. Finally, the temperature of the stirred mixture was raised to 120° C. for 30 minutes. It was then allowed to cool, filtered and washed with abundant water to remove the PhOAc. The resulting solid was dried and gave 50 g. It was dissolved in acetone and precipitated with chloroform, allowed to cool and filtered. The solid formed was dried to yield 30 g of 3,3-bis-(4-hydroxyphenyl)-7-methyl-2 -indolinone, m.p. 272°-4° C. Yield: 52%.

Workup

  1. additionAt the end of the addition
  2. temperaturethe temperature was raised to 85° C.
  3. temperatureFinally, the temperature of the stirred mixture was raised to 120° C. for 30 minutes
  4. temperatureto cool
  5. filtrationfiltered
  6. washwashed with abundant water
  7. customto remove the PhOAc
  8. customThe resulting solid was dried
  9. customgave 50 g
  10. customprecipitated with chloroform
  11. temperatureto cool
  12. filtrationfiltered
  13. customThe solid formed
  14. customwas dried

Sources & evidence

ORD record
ord-0c7136e6d5af4aee81d3e1c5a4576156
Source dataset
uspto-grants-1977_10
Patent number
US04053483

Reaction notes

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