Reacción #742289

Ecuación de reacción

sodium sulfite

oxygen

ozone

isopulegol

isopulegol

→

titled compound

Rendimiento 74.9%

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

Rendimiento 74.9%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente