Phenol → Oxyphenisatin

HRID 2052451Notes

Reaction equation

HRID 2052451 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[OH:18][C:12]1[CH:17]=[CH:16][C:15]([C:4]2([C:15]3[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:1][C:2]2=[O:3])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 7054Isatin

Product 1

HCID 31315OxyphenisatinYield 82%

Conditions

Temperature
85 °C

Procedure

147 g of isatin and 470 g of phenol were brought together and heated to 85° C. Hydrogen chloride gas dried over sulphuric acid is then passed in at 85° C., during which the reaction temperature rises to 115° C. This temperature is maintained and hydrogen chloride is passed in for a further 5 hours. The resulting crystal paste is stirred into 500 ml of benzene and the crystals, colored light yellow, which are thereupon obtained are filtered off and dried. After recrystallization from acetone/chloroform and drying in a water pump vacuum at 90° C., 260 g (82% yield) of colorless crystals are obtained. Melting point 267° C.

Workup

  1. dry with materialHydrogen chloride gas dried over sulphuric acid
  2. customis then passed in at 85° C., during which
  3. customrises to 115° C
  4. temperatureThis temperature is maintained
  5. customis passed in for a further 5 hours
  6. customthe crystals, colored light yellow, which are thereupon obtained
  7. filtrationare filtered off
  8. customdried
  9. customAfter recrystallization from acetone/chloroform
  10. dry with materialdrying in a water pump vacuum at 90° C.

Sources & evidence

ORD record
ord-abb6f545ee67446abcd0ea9b6c742691
Source dataset
uspto-grants-1980_01
Patent number
US04185009

Reaction notes

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