N-Hexyl alcohol

Prepare a Grignard reagent from 24 -5 g. of magnesium turnings, 179 g. (157 ml.) of n-heptyl bromide (Section 111,37), and 300 ml. of di-n-butyl ether (1). Cool the solution to 0° and, with vigorous stirring, add an excess of ethylene oxide. Maintain the temperature at 0° for 1 hour after the ethylene oxide has been introduced, then allow the temperature to rise to 40° and maintain the mixture at this temperature for 1 hour. Finally heat the mixture on a water bath for 2 hours. Decompose the addition product and isolate the alcohol according to the procedure for n-hexyl alcohol (Section 111,18) the addition of benzene is unnecessary. Collect the n-nonyl alcohol at 95-100°/12 mm. The yield is 95 g. 

Di-n-hexyl ether. Use 50 g. (61 ml.) of n-hexyl alcohol (b.p. 156-157°) and 6 g. (3-5 ml.) of concentrated sulphuric acid, and heat until the temperature rises to 180°. Pour the reaction mixture into water, separate the upper layer, wash it twice with 5 per cent, sodium hydroxide solution, then with water, and dry over anhydrous potassium carbonate. Distil from a 50 ml. Claisen flask, and collect the fractions of b.p. (i) 160-221° (17 g.), and (u) 221-223° (17 g.). Reflux fraction (i) with 4 g. of sodium and distil from the excess of sodium 9 - 5 g. of fairly prure n-hexyl ether, fraction (iii), are thus obtained. Combine fractions (ii) and (iii) and distil from a little sodium collect the pure n-hexyl ether (19 g.) at 221 - 5-223°. 

Place 204 g. (249-5 ml.) (2 gram mols) of dry n-hexyl alcohol in a 350 ml. Claisen flask with fractionating side arm. Introduce 5-75 g. (0-25 gram atoms) of clean sodium in small pieces and warm under reflux (as in Fig. Ill, 58, 1 but with dropping funnel omitted ) until all the sodium has reacted (ca. 2 hours). Introduce 39 g. (20 ml.) (0-25 gram... 

Hexanol n-Hexyl alcohol 92 C(3Hi40 m-Xylene 1,.3-Dimethylbenzene 70 QHio... 

If tile high boiling residue is transferred to a small Claisen flask and distilled, some n-hexyl alcohol passes over first, followed by n-hexyl n-caproate (2 g.) at 240-250° (mainly 245°). 

Alcohols. n-Butyl alcohol n-Hexyl alcohol alcohol Benzyl alcohol Glycerol Sucrose. 

Fig. 25. Plot of parameter Ct versus pressure for n-hexyl alcohol dehydration, Eqs. (80) and (81).

It is observed that at room-temperature (300°K), the bonded OH frequency for methyl, ethyl, isopropyl, -butyl, isoamyl and n-hexyl alcohols decreases 30, 35, 44, 49, 44, and 50 cm" 1 respectively. 

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