Hydrochloric Acid → 3-Chlorobenzanthrone

HRID 2082925Notes

Reaction equation

HRID 2082925 reaction equation
[CH:1]1[C:17]2=[C:18]3[C:8]([C:9]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.O.[Cl:20]([O-])(=O)=O.[K+].Cl>C(O)(=O)C>[Cl:20][C:3]1[CH:2]=[CH:1][C:17]2[C:16]3[C:11]([C:9](=[O:10])[C:8]4[C:18]=2[C:4]=1[CH:5]=[CH:6][CH:7]=4)=[CH:12][CH:13]=[CH:14][CH:15]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6697BenzanthroneHCID 6426889Potassium Chlorate

Product 1

HCID 728663-Chlorobenzanthrone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 10g amount of benzanthrone was dissolved in a solvent mixture of 100g acetic acid and 100 g of water. 6 g of potassium chlorate was added to the solution and the mixture was heated and stirred at 90°-95° C for 2 hours. 12 g of conc. hydrochloric acid was added dropwise to the mixture during 1 hour and 20 minutes. After the addition, the mixture was stirred for 1 hour to complete the reaction. The reaction mixture was cooled, filtered, washed with water and dried. The product was recrystallized from chlorobenzene to obtain 3-chlorobenzanthrone having a melting point of 179°-190° C (orange needle crystals).

Workup

  1. temperaturethe mixture was heated
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 1 hour
  4. customthe reaction
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washwashed with water
  8. customdried
  9. customThe product was recrystallized from chlorobenzene

Sources & evidence

ORD record
ord-6535ec19ad3443c196510476a94c4633
Source dataset
uspto-grants-1978_04
Patent number
US04083725

Reaction notes

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