N Amyl alcohol

Equip a 1-litre three-necked flask with a powerful mechanical stirrer, a separatory funnel with stem extending to the bottom of the flask, and a thermometer. Cool the flask in a mixture of ice and salt. Place a solution of 95 g. of A.R. sodium nitrite in 375 ml. of water in the flask and stir. When the temperature has fallen to 0° (or slightly below) introduce slowly from the separatory funnel a mixture of 25 ml. of water, 62 5 g. (34 ml.) of concentrated sulphuric acid and 110 g. (135 ml.) of n-amyl alcohol, which has previously been cooled to 0°. The rate of addition must be controlled so that the temperature is maintained at 1° the addition takes 45-60 minutes. AUow the mixture to stand for 1 5 hours and then filter from the precipitated sodium sulphate (1). Separate the upper yellow n-amyl nitrite layer, wash it with a solution containing 1 g. of sodium bicarbonate and 12 5 g. of sodium chloride in 50 ml. of water, and dry it with 5-7 g. of anhydrous magnesium sulphate. The resulting crude n-amyl nitrite (107 g.) is satisfactory for many purposes (2). Upon distillation, it passes over largely at 104° with negligible decomposition. The b.p. under reduced pressure is 29°/40 mm. 

Di-n-amyl ether. Use 50 g. (61 5 ml.) of n-amyl alcohol (b.p. 136-137°) and 7 g. (4 ml.) of concentrated sulphuric acid. The calculated volume of water (5 ml.) is collected when the temperature inside the flask rises to 157° (after 90 minutes). Steam distil the reaction mixture, separate the upper layer of the distillate and dry it with anhydrous potassium carbonate. Distil from a 50 ml. Claisen flask and collect the fractions of boiling point (i) 145-175° (13 g.), (ii) 175-185° (8 g.) and (iii) 185-190° (largely 185-185-5°) (13 g.). Combine fractions (i) and (u), reflux for 1 hour in a small flask with 3 g. of sodium, and distil from the sodium amyloxide and excess of sodium this yields 9 5 g. of fairly pure n-amyl ether (iv). The total yield is therefore 22 - 5 g. A perfectly pure product, b.p. 184 185°, is obtained by further distillation from a Little sodium. 

Dimethyl ether Methyl ether 101 CoHeO 1-Pentanol n-Amyl alcohol 89 CsHi O... 

The designation Ac signifies acyl-oxygen fission, whereas A1 is alkyl-oxygen fission. When n-amyl alcohol was hydrolyzed in 0-enriched water, the 0 appeared in the product acid rather than the alcohol, showing that alkyl-oxygen fission could not have occurred. Carpenter gives many examples of isotopic studies. 

Amyl ozydhydrat, n. amyl alcohol. -ver-bindung, /. amyl compound. 

A mixture of 5 g of the 21-acetate of SCt-chlorohydrocortisone, 7 g of chloranii and 100 cc of n-amyl alcohol was refluxed for 16 hours, cooled and diluted with ether. The solution was successively washed with water, 5% sodium carbonate solution and water, dried over anhydrous sodium sulfate, filtered and evaporated to dryness under reduced pressure. Chromatographic purification of the residue yielded the 21-acetate of 6-chloro-A -pregnatriene-11 3,17a,21 -triol-3,20-dione. ... 

Finally the mother liquor can be extracted by solvents (such as n-amyl alcohol) or passed through a suitable ion exchange resin. Elution is by mineral salts to yield a crude grade mixture. 

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