Acetic Acid → HCID 57061694, compound

HRID 2057720Notes

Reaction equation

HRID 2057720 reaction equation
[Cl:1][C:2]1[C:12]2[C:13]3C(CC[C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[Na+].[Br-].[C:16](O)(=O)[CH3:17].[C:20]([O:23][C:24](=[O:26])[CH3:25])(=[O:22])[CH3:21]>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.C1C=CC=CC=1>[Cl:1][C:2]1[C:16]2[C:17](=[CH:9][CH:8]=[CH:13][CH:12]=2)[C:21]([C:20]([O:23][C:24]([C:25]2[C:11]3[C:12](=[CH:13][CH:8]=[CH:9][CH:10]=3)[C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:26])=[O:22])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 97507Acenaphthene, 5-chloro- (8CI)HCID 253881Sodium Bromide

Product 1

HCID 57061694HCID 57061694, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 93021Manganese acetate tetrahydrateCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

18.9 g of 5-chloroacenaphthene, 0.4 g of cobalt acetate tetrahydrate, 0.65 g of manganese acetate tetrahydrate, 0.2 g of NaBr, 20 ml of acetic acid, and 40 ml of benzene were charged into a reaction vessel, into which air was blown at a rate of 60 ml/min from a temperature of 65° C. The content was gradually heated up to 80° C. in 26 hours. 14 ml, in total, of acetic anhydride was dropwise added to the reaction system over the reaction time. After completion of the reaction, the solvents were removed by distillation. To residue were added 100 ml of tert-butanol and 500 ml of water dissolving 20 g of NaOH therein, to which was dropwise added 9 g of an aqueous 30% hydrogen peroxide solution at 60°-80° C. 2 hours after the dropping, the tert-butanol was removed by steam distillation. The remaining solution was treated in the same manner as in Example 8 to obtain 19.2 g of 4-chloronaphthalic anhydride in a yield of 83%.

Workup

  1. customwas blown at a rate of 60 ml/min from a temperature of 65° C
  2. customAfter completion of the reaction
  3. customthe solvents were removed by distillation
  4. additionTo residue were added 100 ml of tert-butanol and 500 ml of water dissolving 20 g of NaOH
  5. customat 60°-80° C
  6. custom2 hours after the dropping, the tert-butanol was removed by steam distillation
  7. additionThe remaining solution was treated in the same manner as in Example 8

Sources & evidence

ORD record
ord-3c6ac92cf13f4dea8329690bc7c83df7
Source dataset
uspto-grants-1980_07
Patent number
US04212813

Reaction notes

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