반응 #214427

반응 방정식

n-Hexadecanol

sodium hydride

Allyl bromide

→

ether

수율 50.0%

Allyl-n-hexadecylether

수율 50.0%

용매

dimethylformamide

sodium chloride

반응 조건

후처리

1. 1
   온도the mixture heated to 90° C. for 5 hours
2. 2
   온도The reaction was cooled
3. 3
   추출extracted with ether (2×300 ml)
4. 4
   세척The combined ether extracts were washed with a saturated solution of sodium chloride (200 ml)
5. 5
   여과filtered
6. 6
   건조dried over magnesium sulfate
7. 7
   workup.ADDITIONtreated with activated charcoal
8. 8
   여과filtered
9. 9
   기타evaporated under reduced pressure to an oil
10. 10
    기타The resulting oil was purified
11. 11
    기타by absorbing it on silica gel
12. 12
    여과filter
13. 13
    세척eluting the product off with hexane (7×200 ml)
14. 14
    농축Concentration

실험 절차

n-Hexadecanol (24.2 g, 0.1 mol) was added to a suspension of sodium hydride (9.6 g of a 50% dispersion in mineral oil, 0.2 mol) in dimethylformamide (200 ml) and heated to 50° C. for 30 minutes. Allyl bromide, (24.2 g, 0.2 mol) was then added and the mixture heated to 90° C. for 5 hours. The reaction was cooled, diluted with a solution of saturated sodium chloride (300 ml), and extracted with ether (2×300 ml). The combined ether extracts were washed with a saturated solution of sodium chloride (200 ml), filtered, dried over magnesium sulfate, treated with activated charcoal, filtered, and evaporated under reduced pressure to an oil. The resulting oil was purified by absorbing it on silica gel, placing the silica gel in a sintered glass filter, and eluting the product off with hexane (7×200 ml) followed by toluene (4×200 ml). Concentration yielded the pure ether (14 g, 50% yield): NMR (CDCl3) 3.40 (t, 2, --CH2 --O--CH2CH=CH2), 3.92 (d, 2, --O--CH2CH=CH2), 4.95-5.38 (m, 2, =CH2) and 5.58-6.20 (m, 1, --CH=CH2).

출처