Lauric Acid → 12-Tricosanone

Lauric acid (50 g, 0.25 mol) and magnesium oxide (12.6 g, 0.3125 mol) were charged in a 500 ml round bottom flask equipped with an air condenser having a length of 50 cm, and then the mixture was heated at 300° to 320° C. for 8 hours using a heating mantle. After the completion of the reaction, the reaction solution was cooled. Then, 250-300 ml of n-hexane was added and the reaction solution was sufficiently dissolved in n-hexane with heating. The resulting solution was filtered in a hot state and about 200 ml of an aqueous 4N-sulfuric acid solution was added to the filtrate, followed by sufficiently stirring to decompose unreacted magnesium laurate. The hexane layer was separated, washed with water, and then washed with 200 ml of an aqueous 5% NaOH solution to remove dissolved lauric acid. The hexane layer was washed again with water, dried over anhydrous sodium sulfate and filtered, and then hexane was removed by using a rotary evaporator to isolate a reaction product. The resulting product was recrystallized from a mixed solvent of ethanol and benzene in the ratio of 2:1 to obtain 32.9 g of 12-tricosanone as a white flakelike crystal (yield 77.8%).

1. customequipped with an air condenser
2. temperaturethe mixture was heated at 300° to 320° C. for 8 hours
3. customAfter the completion of the reaction
4. temperaturethe reaction solution was cooled
5. temperaturewith heating
6. filtrationThe resulting solution was filtered in a hot state and about 200 ml of an aqueous 4N-sulfuric acid solution
7. additionwas added to the filtrate
8. customThe hexane layer was separated
9. washwashed with water
10. washwashed with 200 ml of an aqueous 5% NaOH solution
11. customto remove
12. dissolutiondissolved lauric acid
13. washThe hexane layer was washed again with water
14. dry with materialdried over anhydrous sodium sulfate
15. filtrationfiltered
16. customhexane was removed
17. customa rotary evaporator
18. customto isolate a reaction product
19. customThe resulting product was recrystallized from a mixed solvent of ethanol and benzene in the ratio of 2:1

ORD record

ord-dce1e0e9c3254424b833635ee9d8f6f5

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05817839