تفاعل #742289

معادلة التفاعل

sodium sulfite

oxygen

ozone

isopulegol

isopulegol

→

titled compound

المردود 74.9%

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

المردود 74.9%

المذيبات

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر