반응 #602932

반응 방정식

1,3,5-Trioxane

2-Cyclopentylbenzonitrile

dry ice IPA

chlorosulfonic acid

Sulfuric acid

→

title compound

5-(Chloromethyl)-2-cyclopentylbenzonitrile

반응 조건

후처리

1. 1
   기타fitted with an addition funnel and dry nitrogen inlet
2. 2
   workup.ADDITIONwere added fairly quickly
3. 3
   workup.STIRRINGIt was stirred at between 6.9° C. and −5° C. for 1.5 h
4. 4
   기타The reaction was quenched
5. 5
   workup.ADDITIONby slowly pouring into ice water
6. 6
   workup.ADDITIONMTBE was added
7. 7
   workup.STIRRINGthe mixture was stirred well
8. 8
   여과filtered through Celite®
9. 9
   세척The Celite® bed was washed with MTBE
10. 10
    기타the aqueous acid layer was separated
11. 11
    추출The acid layer was extracted with MTBE
12. 12
    세척The combined MTBE layer was washed with water
13. 13
    세척The organic layer was washed with water until washings
14. 14
    건조The organic layer was dried over anhydrous Na2SO4
15. 15
    여과filtered
16. 16
    기타The solvent was removed under reduced pressure
17. 17
    기타The residue was purified by silica gel column chromatography

실험 절차

2-Cyclopentylbenzonitrile (1.3 g, 7.59 mmol) was transferred into a 2-necked RB flask, fitted with an addition funnel and dry nitrogen inlet. The starting material was stirred and cooled to −22° C. (dry ice/IPA bath). Sulfuric acid (3.25 mL, 61.0 mmol) was added in drops. 1,3,5-Trioxane (0.877 mL, 11.39 mmol) was added in 3 batches (The batches were added fairly quickly, one after another). Almost immediately, chlorosulfonic acid (0.915 mL, 13.67 mmol) was added in drops. Then the reaction mixture (dark brown in color) was allowed to warm up to −7° C. (over approx 15 min). It was stirred at between 6.9° C. and −5° C. for 1.5 h. The reaction was quenched by slowly pouring into ice water. MTBE was added and the mixture was stirred well and filtered through Celite®. The Celite® bed was washed with MTBE and the aqueous acid layer was separated. The acid layer was extracted with MTBE. The combined MTBE layer was washed with water followed by saturated NaHCO3 solution. The organic layer was washed with water until washings were neutral to pH paper. The organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound.

출처