반응 #742289

반응 방정식

sodium sulfite

oxygen

ozone

isopulegol

isopulegol

→

titled compound

수율 74.9%

(1R,2R,4R)-1-(2-hydroxy-4-methylcyclohexyl)ethanone

수율 74.9%

용매

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONwas introduced into the reaction solution while the temperature of the solution
3. 3
   기타was being kept between from 15° C. to 23° C
4. 4
   기타The reaction solution obtained
5. 5
   온도was cooled in an ice bath
6. 6
   추출The solution was extracted with toluene
7. 7
   기타The toluene solution obtained
8. 8
   세척was sequentially washed with dilute hydrochloric acid
9. 9
   건조an aqueous sodium carbonate solution, an aqueous ammonium chloride solution and brine, and was dried over anhydrous sodium sulfate
10. 10
    여과After filtration
11. 11
    기타the solvent was removed by evaporation under a reduced pressure
12. 12
    기타The mixture obtained
13. 13
    기타was crystallized
14. 14
    workup.ADDITIONby adding 350 ml of heptane
15. 15
    기타the crystal obtained
16. 16
    세척was washed with 50 ml of cold heptane
17. 17
    기타by drying under vacuum

실험 절차

To a 500 ml reaction vessel, 70.0 g (453.8 mmol) of isopulegol and 140 ml of methanol were added and ozone generated in an oxygen stream by silent discharge was introduced into the reaction solution while the temperature of the solution was being kept between from 15° C. to 23° C. After 10 hours, disappearance of the raw material, isopulegol was confirmed by the gas chromatogram. The reaction solution obtained was cooled in an ice bath and then added into an excess amount of an aqueous sodium sulfite solution at a temperature of 30° C. or lower, followed by stirring for 2 hours. The solution was extracted with toluene. The toluene solution obtained was sequentially washed with dilute hydrochloric acid, an aqueous sodium carbonate solution, an aqueous ammonium chloride solution and brine, and was dried over anhydrous sodium sulfate. After filtration, the solvent was removed by evaporation under a reduced pressure. The mixture obtained was crystallized by adding 350 ml of heptane, and the crystal obtained was washed with 50 ml of cold heptane followed by drying under vacuum to obtain 53.08 g (yield: 74.9%) of the titled compound as a colorless needle crystal.

출처