Water → HCID 20227941, compound

HRID 1824561Notes

Reaction equation

HRID 1824561 reaction equation
CN(C=O)C.B.[Na].O.S(=O)(=O)(O)O.[CH:14]12[CH2:20][CH:17]([CH:18]=[CH:19]1)[CH:16]1[C:21]([O:23][C:24](=O)[CH:15]21)=[O:22]>[Cl-].[Na+].O>[C:17]12[CH2:20][CH:14]([CH2:19][CH2:18]1)[CH:15]1[C:16]=2[C:21](=[O:22])[O:23][CH2:24]1

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 6228Dimethylformamide3×HCID 13223826-62-03×HCID 178418435HCID 178418435, compound2×

Product 1

HCID 20227941HCID 20227941, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

18.0 kg of DMF and 1.17 kg (27.8 mol) of sodium boron hydride were placed in a 200 L glass lining reaction tank equipped with a jacket and an agitator, and sodium boron hydride was dissolved by stirring. Thereafter, brine was supplied to the jacket, and the inside of the tank was set at a temperature of 0° C. to 5° C. Moreover, nitrogen gas started to be supplied at 0.1 L/min from the end of the tank. 8.46 kg (51.5 mol) of a commercially available 5-norbornene-2,3-dicarboxylic anhydride and 12.7 kg of DMF were placed in a 25 L dissolution tank, and 5-norbornene-2,3-dicarboxylic anhydride was completely dissolved by stirring. Using a proportioning pump, the prepared DMF solution comprising 5-norbornene-2,3-dicarboxylic anhydride was fed to the reaction tank, while paying attention so that the internal temperature of the tank did not exceed 30° C. After completion of the feeding, while maintaining the internal temperature of the tank at 5° C. to 15° C., stirring was continued for 2 hours. 80 kg of water was slowly fed thereto so that the internal temperature did not exceed 30° C. Then, concentrated sulfuric acid was slowly fed thereto until the pH became 0.5, and stirring was continued for 3 hours. Subsequently, the supply of nitrogen gas was stopped, the solution was extracted twice with 40 kg of MIBK, and the combined organic extracts were washed with 45 kg of water. The organic layers were concentrated at 50° C. at 6.6 kPa, until the MIBK concentration in the solution became about 50% by weight. An aliquot of the concentrate was collected, and it was analyzed by gas chromatography. As a result, 6.90 kg (45.9 mol) of 4-oxatricyclo[5.2.1.02,6]decen-3-one was obtained at a yield of 89%. The MIBK concentration was 57%. Thereafter, the content in the tank was transferred to a 25 L container. This time, the solution had good flowability, and so the solution was eliminated from the reaction tank without any problem.

Workup

  1. customequipped with a jacket
  2. customwas set at a temperature of 0° C. to 5° C
  3. dissolutionwas completely dissolved
  4. stirringby stirring
  5. customdid not exceed 30° C
  6. temperatureAfter completion of the feeding, while maintaining the internal temperature of the tank at 5° C. to 15° C.
  7. stirringstirring
  8. customdid not exceed 30° C
  9. stirringstirring
  10. waitwas continued for 3 hours
  11. extractionthe solution was extracted twice with 40 kg of MIBK
  12. washthe combined organic extracts were washed with 45 kg of water
  13. concentrationThe organic layers were concentrated at 50° C. at 6.6 kPa, until the MIBK concentration in the solution
  14. customAn aliquot of the concentrate was collected

Sources & evidence

ORD record
ord-dfb20d9148eb4df0b86f6b54816bdb0f
Source dataset
uspto-grants-2006_05
Patent number
US07041838B2

Reaction notes

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