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Acetic Anhydride → HCID 57151183, compound

HRID 2057719
Notes
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Reaction equation

HRID 2057719 reaction equation
[Cl:1][C:2]1[C:12]2[C:13]3C(CC[C:8]=3[CH:9]=[CH:10][C:11]=2[Cl:14])=[CH:4][CH:3]=1.[C:15]([O:18][C:19](=[O:21])[CH3:20])(=[O:17])[CH3:16].[OH-].[K+].Cl[O-].[Na+]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.[Na+].[Br-].O.ClC1C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[C:12]2[C:13](=[CH:8][CH:9]=[CH:10][C:11]=2[Cl:14])[C:16]([C:15]([O:18][C:19]([C:20]2[C:13]3[C:12](=[C:11]([Cl:14])[CH:10]=[CH:9][CH:8]=3)[C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:21])=[O:17])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 4

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 1457305,6-Dichloro-1,2-dihydroacenaphthyleneHCID 23665760Sodium Hypochlorite

Product 1

HCID 57151183HCID 57151183, compoundYield 88%

Reagents, catalysts & solvents 6

HCID 61372
Cobalt(II) acetate tetrahydrate
Catalyst
HCID 93021Manganese acetate tetrahydrateCatalyst
HCID 253881Sodium BromideCatalyst
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent
HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
65 °C

Procedure

There was provided a 300 ml flask which was equipped with an agitator and a thermometer and provided with a gas feed port and a gas exhaust port attached with a condenser. The flask was charged with 22.3 g of 5,6-dichloroacenaphthene, 0.6 g of cobalt acetate tetrahydrate, 0.2 g of manganese acetate tetrahydrate, 0.2 g of NaBr, 10 ml of acetic acid, 90 ml of chlorobenzene, and 17 ml of acetic anhydride. The reaction system was heated to 65° C., into which air was blown for oxidation at a rate of 50 ml/min. The reaction was continued for 20 hours, during which the system was gradually heated up to 95° C. After completion of the reaction, the acetic acid was removed by distillation together with the chlorobenzene. To the remaining reaction mixture were added 50 ml of chlorobenzene and 400 ml of water dissolving therein 27 g of KOH, into which 32 ml of a sodium hypochlorite solution (13.6%) was dropped at 70°-100° C. The chlorobenzene was removed from the reaction solution, followed by treating with active carbon and filtering. The filtrate was treated with an acid to permit precipitation and the precipitate was filtered, washed with water and dried to obtain 23.5 g of 4,5-dichloronaphthalic anhydride. The yield was 88.0%.

Workup

  1. customThere was provided a 300 ml flask which
  2. customwas equipped with an agitator
  3. customa thermometer and provided with a gas feed port
  4. customattached with a condenser
  5. temperaturethe system was gradually heated up to 95° C
  6. customAfter completion of the reaction
  7. customthe acetic acid was removed by distillation together with the chlorobenzene
  8. customTo the remaining reaction mixture
  9. customThe chlorobenzene was removed from the reaction solution
  10. additionby treating with active carbon
  11. filtrationfiltering
  12. additionThe filtrate was treated with an acid
  13. customprecipitation
  14. filtrationthe precipitate was filtered
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-cd47e84624ac4461887805ce5a767c80
Source dataset
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04212813

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes