80 



ALCOHOLS 



[22-23 A. 



255 ; Erlenmeyer and Hell, Ann. 16O, 

 275; Le 7, Ber - 6, 1363; LeBel, 

 Bull. Soc. [2] 25, 545 ; Just, Ann. 

 220, 148 ; Udranszky, Zeit. physiol. 

 Ch. 13, 251 : for method of separa- 

 tion of amyl alcohols of fusel oil see 

 Marckwald, Ber. 34, 479; 485; 35, 



1595)- 



Its production during fermentation 

 has been attributed to bacteria asso- 

 ciated with the yeast ; this alcohol is 

 not obtained with pure cultures of ellip- 

 tical yeast (Gentil, Mon. Sci. [4] 11, 

 II, 568; Ch. Centr. 1897, 2, 622). 

 Saccharomyces anomalus of Hansen pro- 

 duces amyl acetate during fermentation 

 (Barker, Ann. Bot. 1900, 215). 



An ester (amyl or isoamyl) of valeric 

 acid is among the products of decom- 

 position of albumin (peptone) by Bacil- 

 lus prfepollens from the intestine (Maas- 

 sen, Ch. Centr. 1899, 2, 1059). An 

 amyl (? isoamyl) alcohol occurs as ester 

 in rancid fat, probably as a bacterial 

 product (Nagel, Am. Ch. Journ. 23, 

 173). An amyl (? isoamyl) alcohol is 

 among the products of hydrolysis and 

 fermentation of starch by the Bacillus 

 amylozymicus of Perdrix (Ann. Inst. 

 Past. 5, 287). 



A ' fusel oil ' (alcohols not identified) 

 is said to occur in milk from cows fed 

 with ' slump' (Teichert, Bied. Centr. 

 31, 2io ; Journ. Ch. Soc. 82, II, Abst. 

 348). 



SYNTHETICAL PROCESSES. 



[A.] From isovaleric aldehyde (2- 

 methyl-4-butanal) [95] by reduction 

 with sodium amalgam (Friedel, Ann. 

 124, 326 ; Balbiano, Ber. 9, 1437 and 

 1692 ; Gazz. 6, 229 ; Erlenmeyer, Ann. 

 Suppl. 5, 337; Wurtz, Ann. 134, 201). 

 Also from isovaleric aldehyde (with 

 other products) by heating with lime 

 (Fittig, Ann. 117, 68). 



[B.] From isovaleric acid [Vol. II] 

 by conversion into the chloride ana 

 reduction of the latter with sodium in 

 moist ethereal solution (W. H. Perkin, 

 junr., and Sudborough, Proc. Ch. Soc. 

 10, 216). 



23. Normal Hexyl Alcohol; 

 1-Hexaiiol. 



CH 3 .[CH 2 ] 4 .CH 2 .OH 



NATURAL SOURCES. 



As ester of acetic acid in oil from 

 Heracleum sphondylium (Moslinger, Ber. 

 9, 998 ; Ann. 185, 2,6), and as ester 

 of butyric acid in oil of Heracleum 

 giganteum (Franchimont and Zincke, 

 Ber. 4, 822 ; Ann. 163, 193). Hexyl 

 alcohol (? normal) exists as ester in the 

 ethereal oil from the root of Aspidium 

 filix mas (Ehrenberg, Arch. Pharm. 

 231, 345). A caproyl (? n-hexyl) al- 

 cohol occurs as ester in rancid fat, 

 probably a bacterial product (Nagel, 

 Am. Ch. Journ. 23, 173). It is not 

 certain that the alcohol from any of 

 these sources is the normal alcohol. 

 A hexyl alcohol occurs in fusel oil from 

 brandy (Faget, Ann. 88, 325 ; Ordon- 

 neau, Comp. Rend. 102, 217). 



SYNTHETICAL PROCESSES. 



[A.] From normal propyl alcohol [15] 

 through n-hexane by the action of 

 sodium on n-propyl iodide (Schorlem- 

 mer, Phil. Trans. 162, 118; Ann. 161, 

 277; Briihl, Ann. 2OO, 183; Stoh- 

 mann, Journ. pr. Ch. [2] 43, 7 ; Mi- 

 chael, Ber. 34, 4036), n-hexyl chloride 

 which is formed (with secondary hexyl 

 chloride) by chlorination (Cahours, 

 Comp. Rend. 10, 1241 ; Jahresber. 

 1863, 525), and then through the ace- 

 tate and hydrolysis (Cahours and 

 Pelouze, Comp. Rend. 54, 1245 ; Schor- 

 lemmer, Ann. 161, 272). 



Normal hexane is capable of being 

 directly nitrated, and the mononitro- 

 derivative on reduction gives n-hexyl- 

 amine [Vol. II] (Worstall, Am.Ch. Journ. 

 20, 202; 21,2io; 218), which can be 

 converted into the alcohol as under G-. 



NOTE : Certain aromatic compounds such as 

 benzene [6] ; styrene [7] ; phenol [60] ; benzoic acid 

 [Vol. II] ; alizarin [1451, &c., are said to give 

 hexane among the products of reduction by 

 strong aqueous hydriodic acid at a high tem- 

 perature (Berthelot, as under methane [1 ; I] : 

 see also v. Baeyer, Ann. 155, 266 ; Wredin, 



