Ethanol → HCID 21205052, compound

HRID 2052452Notes

Reaction equation

HRID 2052452 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:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[CH2:23]([OH:25])[CH3:24].[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(Cl)(Cl)Cl.[CH3:37][C:38](C)=O>>[OH:22][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:4]2([C:37]3[C:26]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:23]([OH:25])=[CH:24][CH:38]=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

6

Reactant 5

HCID 702EthanolHCID 996PhenolHCID 70051-NaphtholHCID 7054IsatinHCID 15930782Chloroform acetone

Product 1

HCID 21205052HCID 21205052, compoundYield 80%

Conditions

Temperature
100 °C

Procedure

147 g of isatin and 720 g of α-naphthol are brought together and initially heated to 100° C. Hydrogen chloride gas dried over sulphuric acid is then passed in, during which the temperature rises to 150° C. After the exothermic reaction has subsided the reaction temperature is maintained at 115° C. for a further 5 hours and after cooling, 1,000 ml of ethanol are added to the solidified crystal mass. The crystals, freed from excess phenol, are filtered off and dried. 334 g (80% yield) of colorless crystals are obtained from chloroform/acetone. Melting point 300° C., with decomposition.

Workup

  1. dry with materialHydrogen chloride gas dried over sulphuric acid
  2. customrises to 150° C
  3. customAfter the exothermic reaction
  4. temperatureis maintained at 115° C. for a further 5 hours
  5. temperatureafter cooling
  6. filtrationare filtered off
  7. customdried

Sources & evidence

ORD record
ord-eec85b300b0e4925b6000f995111be84
Source dataset
uspto-grants-1980_01
Patent number
US04185009

Reaction notes

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