반응 #68723

반응 방정식

HCl

2-norbornanone

o-cresol

MeOH

MeOH

o-cresol

1-dodecanethiol

MeOH

o-cresol

→

product

수율 75.0%

4,4′-(bicyclo[2.2.1]heptane-2,2-diyl)bis(2-methylphenol)

수율 75.0%

반응 조건

후처리

1. 1
   기타equipped
2. 2
   기타reaction vessel
3. 3
   workup.ADDITIONAfter addition
4. 4
   기타the HCl gas was bubbled for another 45 min
5. 5
   workup.STIRRINGThe reaction mixture was stirred for another 17 h at 40° C.
6. 6
   온도The mixture was cooled to room temperature
7. 7
   기타removed
8. 8
   기타MeOH using rotary evaporator
9. 9
   workup.ADDITIONdiluted with 50 mL CH2Cl2
10. 10
    여과Filter the white precipitate
11. 11
    세척washed with (3×50 mL) CH2Cl2
12. 12
    기타dried under vacuum for 6 h

실험 절차

An appropriately sized and equipped reaction vessel was charged with o-cresol (44 g, 0.406 mol) in 10 mL MeOH and 1-dodecanethiol (1.09 mL, 0.0045 mol). The mixture was heated to 40° C. and the addition funnel was charged with 2-norbornanone (5 g, 0.045 mol) in 5 mL MeOH and o-cresol (5 g, 0.046 mol) in 5 mL MeOH. The o-cresol solution was added dropwise at 40° C. over 45 min, while introducing HCl gas under stirring. After addition, the HCl gas was bubbled for another 45 min and white precipitate was observed and color turns to light pink from dark orange. The reaction mixture was stirred for another 17 h at 40° C., GC analysis showed no starting material 2-norbornanone. The mixture was cooled to room temperature and removed MeOH using rotary evaporator and diluted with 50 mL CH2Cl2. Filter the white precipitate and washed with (3×50 mL) CH2Cl2 and dried under vacuum for 6 h gave 10.5 g (75% yield) of product as white solid with >99.9% purity by HPLC. 1HNMR, 13CNMR and MS were consistent with the structure.

출처