Cetyl Alcohol → Allylhexadecyl ether

Temperatur

50 °C

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).

1. temperaturethe mixture heated to 90° C. for 5 hours
2. temperatureThe reaction was cooled
3. extractionextracted with ether (2×300 ml)
4. washThe combined ether extracts were washed with a saturated solution of sodium chloride (200 ml)
5. filtrationfiltered
6. dry with materialdried over magnesium sulfate
7. additiontreated with activated charcoal
8. filtrationfiltered
9. customevaporated under reduced pressure to an oil
10. customThe resulting oil was purified
11. customby absorbing it on silica gel
12. filtrationfilter
13. washeluting the product off with hexane (7×200 ml)
14. concentrationConcentration

ORD-Eintrag

ord-4ef50ffc7ba94320958ccede8595d1ab

Quelldatensatz

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04255426