Hexadecyl Iodide

When a poorer grade of cetyl alcohol is used, the yield may be reduced to as low as 70 per cent. 

This material is probably pure enough for most work. Melting points as high as 25° are recorded in the literature. 

Traces of iodine come over when the distillation starts and the fore-run is therefore strongly colored. When distillation is started again after being interrupted traces of iodine again appear in the first few drops of the main distillate. A more nearly colorless distillate is obtained if means are provided for cutting fractions without interrupting the distillations. 

The method described is essentially that of Smith.1 Several other workers have used a similar method.2 Cetyl iodide has also been prepared by heating cetyl alcohol with yellow phosphorus and iodine in carbon disulfide solution,3 and by repeatedly passing dry hydrogen iodide acid into the molten alcohol and permitting the reaction mass to stand between additions.4 

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Hexadecyl iodide [544-77-4] Hexafluoroisobutylene Daphnia pulex EC50 (48-h) -0.66 Passino and Smith, 1987... 

The carbamate ester derivatives of 2,3-bornanediol 11 and 12 were alkylated by treatment with lithium cyclohexylisopropylamide in tetrahydrofuran at —8013 C and subsequent addition of hexadecyl iodide or iodomethane. respectively, in the presence of HMPA. Chemical yields were 90% and the diastereomeric ratios 13a/13b were 93 7 and 10 90, respectively117. 

The commonest method of reduction can be illustrated by the preparation of /i-hexadecane from hexadecyl iodide 430... 

A mixture of glacial acetic acid (915 ml), zinc dust (327 g), and hexadecyl iodide (352 g) is saturated with dry hydrogen chloride in a round-bottomed flask (21) fitted with a stirrer and a gas inlet tube. The mixture is then heated, with stirring, on a steam-bath, saturated again with hydrogen chloride after 5 h, and after 25 h allowed to cool. The upper layer, consisting of hexadecane, is separated. The residual mixture is added to water (3 1), and the zinc dust is filtered off and washed with water (500 ml) and ether (250 ml). The united aqueous filtrates are washed with ether (2 x 500 ml), and the hexadecane previously separated is dissolved in these extracts. The total ethereal solution is shaken with 20% sodium hydroxide solution (2 x 250 ml), washed with water until free from alkali, dried with anhydrous sodium sulfate (150 g), and, after the ether has been distilled off, is fractionated in a vacuum through a column. -Hexadecane, b.p. 156—158°/14 mm, m.p. 16-17°, is obtained in 85% yield (192 g). 

Secondary and tertiary alcohols are allowed to react for about 8 hours at 0-5° and then further at room temperature, but for preparation of primary iodides the mixtures must be heated finally for several hours at temperatures above 100°, as detailed in Organic Syntheses940 for the preparation of hexadecyl iodide from cetyl alcohol. 

Hexadecyl hexadecanoate, H-00206 Hexadecyl iodide, see 1-00060 Hexadecyl octadecanoate, H-00207 3-Hcxadecyloxy-1,2-propanediol, H-00208... 

Mercuri-cetyl iodide (Mercuri-hexadecyl iodide)... 

Hexadecyl bromide see 1-Bromohexadecane Hexadecyl chloride see 1-Chlorohexadecane Hexadecyl iodide see 1-Iodohexadecane Hexadeuteroacetone see (2H6)Propan-2-one Hexadeuterobenzene see (2H6)Benzene Hexadeuteropropan-2-one see (2H6)Propan-2-one Hexa-1,5-diene Hexafluorobenzene syn. Perlluorobenzene Hexafluoroethane... 

The first C -labeled glyceryl ether was synthesized by Bergstrom and Blomstrand (1956). They obtained 1-C -hexadecyl glyceryl ether by reacting the C -hexadecyl iodide with allyl alcohol and sodium, lire allyl hexadecyl ether was hydroxylated by use of hydrogen peroxide in glacial acetic acid, yielding a product with a specific activity of 10 cpm/mg. 

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