Hexyl Alcohol, 506,

In a 5-I. round-bottom flask, fitted with a stirrer, separatory funnel and a reflux condenser to the upper end of which a calcium chloride tube is attached, is placed 150 g. of magnesium turnings. A small crystal of iodine (Note i) and about 100 cc, of a mixture of 822 g. (6 moles) of M-butyl bromide and 2 1. of anhydrous ethyl ether are added. As soon as the reaction starts, 350 cc. of anhydrous ether is added and the remainder of the -butyl bromide solution is dropped in at such a rate that the mixture boils continuously. The time of addition (one and one-half hours) may be decreased by cooling the flask externally. Stirring is started as soon as enough liquid is present in the flask. 

When all has been added (Note 2), 278 g. (6.3 moles) of ethylene oxide (Note 3) (previously dried with soda lime) is added through a tube (3 or 4 mm. in diameter) the end of which is about 20 mm. above the surface of the liquid (Note 4), the temperature being kept below 10° by cooling in an efficient ice-and-salt bath (Note 5). This addition requires four to six hours. When all has 

The reaction between the ethereal solution of butyl bromide and the magnesium frequently starts without any assistance, but the presence of a trace of iodine is of no disadvantage and renders more certain the beginning of the reaction. 

The butyl bromide appears to react as fast as it is added, so that there is no need of stirring or warming the butylmag-nesium bromide solution before adding the ethylene oxide. The small amount of unattacked magnesium has no influence on the subsequent reactions. 

A convenient arrangement consists of placing the ethylene oxide tank on suitable scales and noting the proper decrease in weight. The gas may be passed through a short tower filled with soda lime and then through a spiral condenser surrounded with salt and ice. 

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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. 

Place 179 g. (109-5 ml.) of redistilled thionyl chloride in the 250 ml. Claisen flask and 51 g. (62-6 ml.) of n-hcxyl alcohol, b.p. 156-158°, in the separatory funnel. Add the nr-hexyl alcohol during 2 hours there is a slight evolution of heat, sulphur dioxide is evolved (hence carry out the... 

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... 

Alcohols. Ji-Butyl alcohol ji-Hexyl alcohol [Pg.1056]

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

M-Hexyl alcohol has been prepared by the reduction of ethyl caproate by means of sodium and absolute alcohoB alone or in anhydrous ammonia solution by the reduction of -caproamide by means of sodium and absolute alcohol by the reduction of -caproaldehyde by means of sodium amalgam in dilute sulfuric acid and by means of living yeast, It has also been produced by the action of nitrous acid upon w-hexylamine by the action of sodium upon a mixture of ethyl alcohol and M-butyl alcohol ... 

C6H4CL2 P-DICHLORO- 21.345 1.8209E-01 1.0115E-05 77.15 281 C6H140 HEXYL-ALCOHOL -322.910 6.0346E-01 5.1175E-05 -137.95... 

The M-hexyl bromide may be prepared from redistilled -hexyl alcohol by the red phosphorus-bromine procedure or may be purchased from Eastman Kodak Company. 

Chemical Designations - Synonyms 2-Ethyl-1-butanol 2-Ethylbutil alcohol sec-Hexyl alcohol sec-Pentyl carbinol Pseudohexyl alcohol Chemical Formula (CjHj)2CHCH20H. 

Chemical Designations - Synonyms-. Amylcarbinol 1-Hexanol Hexyl alcohol 1-Hydroxyhexane Chemical Formula CH3(CH2)4CHjOH. 

Normal hexyl alcohol, CH. CHj. CHj. CHo. CHj. CHjOH, is found, principally in the form of esters, in a few essential oils, especially the oil... 

Of these phenyl-amyl alcohol has a pleasant, but somewhat evanescent lemon-like odour phenyl-hexyl alcohol has a very similar odour to this and phenyl-heptyl alcohol has a slight, but extremely agreeable odour [Pg.129]

Ethylhexylene glycol Octoic acid 2-Ethyl hexyl alcohol Octyl acetate... 

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