Water → HCID 20227941, compound

Participants

Reaction Steps

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.

Provenance & Evidence