反応 #214427

反応方程式

n-Hexadecanol

sodium hydride

Allyl bromide

→

ether

収率 50.0%

Allyl-n-hexadecylether

収率 50.0%

溶媒

dimethylformamide

sodium chloride

反応条件

後処理

1. 1
   温度the mixture heated to 90° C. for 5 hours
2. 2
   温度The reaction was cooled
3. 3
   抽出extracted with ether (2×300 ml)
4. 4
   洗浄The combined ether extracts were washed with a saturated solution of sodium chloride (200 ml)
5. 5
   ろ過filtered
6. 6
   乾燥dried over magnesium sulfate
7. 7
   workup.ADDITIONtreated with activated charcoal
8. 8
   ろ過filtered
9. 9
   その他evaporated under reduced pressure to an oil
10. 10
    その他The resulting oil was purified
11. 11
    その他by absorbing it on silica gel
12. 12
    ろ過filter
13. 13
    洗浄eluting the product off with hexane (7×200 ml)
14. 14
    濃縮Concentration

実験手順

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).

出典