Oxygen → Naphthalene-1-carbonyl naphthalene-1-carboxylate

HRID 2057721Notes

Reaction equation

HRID 2057721 reaction equation
C1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=C3C1.[Na+].[Br-].N([CH2:22][CH2:23]O)(CCO)CCO.O=O.[C:27]([O:30][C:31](=[O:33])[CH3:32])(=[O:29])[CH3:28]>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.ClC1C=CC=CC=1.C(O)(=O)C>[C:28]1([C:27]([O:30][C:31]([C:32]2[C:8]3[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=2)=[O:33])=[O:29])[C:22]2[C:23](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:9][CH:8]=1

Participants

10

Reactant 5

HCID 977Oxygen2×HCID 6734AcenaphtheneHCID 7618TriethanolamineHCID 7918Acetic Anhydride2×HCID 253881Sodium Bromide

Product 1

HCID 350399Naphthalene-1-carbonyl naphthalene-1-carboxylateYield 79%

Reagents, catalysts & solvents 4

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 93021Manganese acetate tetrahydrateCatalystHCID 176Acetic AcidSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
65 °C

Procedure

8 g of acenaphthene, 0.45 g of cobalt acetate tetrahydrate, 0.045 g of manganese acetate tetrahydrate, 0.045 g of NaBr, 0.17 ml of triethanolamine, 30 ml of acetic acid, and 50 ml of chlorobenzene were charged in the same manner as in Example 1. The air in the system was substituted with oxygen gas and the system was heated to 65° C., the reaction setting in. Acetic anhydride was dropped while gradually heating the reaction system for reaction. The reaction was continued for 42 hours during which the reaction temperature was increased up to 90° C. The total amount of absorbed oxygen reached 3170 ml and acetic anhydride was added in an amount of 7 ml. After completion of the reaction, the reaction mixture was cooled to allow crystals to precipitate and the crystals were separated by filtration, washed with water and dried to obtain 8.1 g of yellowish white naphthalic anhydride (yield 79%).

Workup

  1. temperaturewhile gradually heating the reaction system
  2. customfor reaction
  3. temperaturethe reaction temperature was increased up to 90° C
  4. additionwas added in an amount of 7 ml
  5. customAfter completion of the reaction
  6. temperaturethe reaction mixture was cooled
  7. customto precipitate
  8. customthe crystals were separated by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-f8b6c5542e7f47b7b3d3619b5b431772
Source dataset
uspto-grants-1980_07
Patent number
US04212813

Reaction notes

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