반응 #3860

반응 방정식

carbonate

potassium carbonate

1,4-dioxane

(Z,Z)-11,13-hexadecadienal

→

(Z,Z)-1,12,14-heptadecatriene

용매

water

반응 조건

후처리

1. 1
   기타was prepared in a 100 ml round bottomed flask
2. 2
   기타equipped with a magnetic stirrer
3. 3
   온도thermometer and reflux condenser
4. 4
   온도The mixture was heated
5. 5
   온도to reflux at 105°-110°
6. 6
   기타were withdrawn periodically
7. 7
   기타partitioned between 1 ml of H2O and 1 ml of hexane
8. 8
   기타at 1.1 and 2.2 and 17 hr
9. 9
   workup.ADDITIONMore potassium carbonate (1.7 g) was added at 212 hr
10. 10
    기타the reaction to completion
11. 11
    온도The reaction mixture was cooled
12. 12
    추출extracted 3 times with 25 ml of hexane
13. 13
    추출the organic layer was extracted with water
14. 14
    기타dried
15. 15
    기타the solvent removed

실험 절차

(Z,Z)-1,12,14-heptadecatriene (TRIENE) was synthesized conveniently from Wittig Salt and aldehyde in aqueous dioxidepotassium carbonate heterogeneous medium (Lechat 1982). A mixture of 3.57 g (0.01 mol) of methyl triphenylphosphonium bromide (Alfa Inorganics), 1.7 g (0.14 mol) of potassium carbonate, 10 ml of 1,4-dioxane, 0.15 ml of water and 2.36 g (0.01 mol) of (Z,Z)-11,13-hexadecadienal (AL. Albany International) was prepared in a 100 ml round bottomed flask equipped with a magnetic stirrer, thermometer and reflux condenser. The mixture was heated to reflux at 105°-110° with stirring while aliquots of 15 ul were withdrawn periodically and partitioned between 1 ml of H2O and 1 ml of hexane. Analysis by gas-liquid chromatography, showed 66, 70 and 99% triolefin and 30%, 26% and 1% starting aldehyde at 1.1 and 2.2 and 17 hr, respectively. More potassium carbonate (1.7 g) was added at 212 hr to drive the reaction to completion. The reaction mixture was cooled and extracted 3 times with 25 ml of hexane, then the organic layer was extracted with water, dried and the solvent removed to leave 1.8 g of yellow oil and a few crystals of triphenylphosphine oxide. The oil was taken up in hexane and passed through a 1×45 cm column of silica gel (60-200 mesh, Baker) with hexane, to yield 1.7 g (73% yield) of clear oil.

출처