20 B-31 A.] 



NONYL ALCOHOL 



85 



a nonyl alcohol (Louren9o and Aguiar, 

 Zeit. [2] 6, 404). 



[C.] From ethyl alcohol [14] and 

 cenanthol [97] by the action of zinc 

 ethyl on the aldehyde and decomposition 

 of the product by water. The alcohol 

 is ethylhexyl carbinol = 3 - nonanol 

 (Wagner, Journ. Russ. Soc. 16, 306; 

 Bull. Soc. [2] 42, 330). 



Or from ethyl alcohol and cenanthol 

 by converting the latter into n-heptyl 

 alcohol [26]. A mixture of n-heptyl 

 and ethyl alcohols gives (among other 

 products) n-nonyl alcohol when heated 

 with sodium to 230 (Guerbet, Comp. 

 'Rend. 135, 172; Bull. Soc. [3] 27, 

 1036). 



[D.] From ethyl alcohol [14] and 

 butyric acid [Vol. III. The latter on 

 distillation of the calcium salt (Chancel, 

 Ann. 52, 295; Kurtz, Ann. 161, 205; 

 Schmidt, Ber. 5, 597), or by the action 

 of ferric chloride on butyryl chloride 

 and decomposition of the product with 

 water (Hamonet, Bull. Soc. [2] 50, 

 358), gives dipropyl ketone = butyrone 

 = 4-heptanone. The latter on treat- 

 ment with zinc and ethyl iodide yields 

 ethyldipropyl carbinol = 4-ethyl-4-hep- 

 tanol (Tschebotareff and Saytzeff , Journ. 

 pr. Ch. [2] 83, 198). 



NOTE : Dipropyl ketone can also be prepared 

 from n-propyl alcohol [15] and butyric acid by the 

 interaction of zinc propyl and butyryl chloride 

 (Schtscherbakoff, Journ. Euss. Soc. 13, 346). Or 

 from butyric acid by heating butyric anhydride 

 with sodium butyrate (Perkin, Trans. Ch. Soo. 

 49, 325) or (among other products) by the action 

 of sodium on ethyl butyrate (Briiggemann, 

 Ann. 246, 140). This ketone is also among 

 the products of the action of zinc on a mixture 

 of butyryl chloride and ethyl ether (Freund, 

 Ann. 118, 33). 



Secondary Nonyl Alcohol. 



A secondary nonyl alcohol (methyl-n- 

 heptyl carbinol) occurs partly free and 

 partly as ester of acetic acid in Algerian 

 oil of rue (v. Soden and Henle, Pharm. 

 Zeit. 46, 1026; Ch. Centr. 1902, 1, 

 256 ; Ch. Drug., 60, 304 ; Power 

 and Lees, Trans. Ch. Soc. 81, 1592). 

 This alcohol has been obtained by re- 

 ducing the corresponding ketone [108] 

 (Mannich, Ber. 35, 2144; Houben, 

 Ibid. 3589). 



30. Secondary Heiiclecatyl or 



Hendecyl Alcohol ; Methyl-n-nonyl 



Carbinol. 



CH 3 \ /H 



CTT f \/"\TT 



nClig 'Ml 



NATURAL SOURCE. 



Occurs partly free and partly as ester 

 of acetic acid in Algerian oil of rue (v. 

 Soden and Henle, Pharm. Zeit. 46, 

 1026; Ch. Centr. 1902, 1, 256; 

 Ch. Drug., 60, 304; Power and Lees, 

 Trans. Ch. Soc. 81, 1593). 



SYNTHETICAL PROCESS. 



[A.] From methylnonyl ketone [109] 

 by reduction with sodium amalgam 

 (Giesecke, Zeit. [2] 6, 428 ; Mannich, 

 Ber. 35, 2144; Houben, Ibid. 3590). 



31. Normal Primary Dodecyl 

 Alcohol; 1-Dodecanol. 



CH 3 .[CH 2 ] 10 .CH 2 .OH 



NATURAL SOURCES. 



Esters of this alcohol (probably stea- 

 rate and palmitate of the normal alcohol) 

 exist in Cascara sagrada (Dohme and 

 Engelhardt, Journ. Am. Ch. Soc. 20, 

 539). Occurs also as ester (of oleic 

 and doeglic acids) in sperm oil and in 

 oil from the bottle-nose whale, and to a 

 small extent in spermaceti [33] (Heintz, 

 Ann. 84, 306; 92, 299; Allen, in 

 Thorpe's ' Diet, of Applied Chem.' Ill, 

 20; Hammarsten's f Lehrb. d. physiol. 

 Chem/ 1895, p. 76). 



SYNTHETICAL PROCESS. 



[A.] From lauric acid [Vol. II] through 

 the aldehyde by distilling the barium salt 

 with barium formate (Krafft, Ber. 13, 

 1414), reduction with zinc dust and 

 acetic acid, and hydrolysis of the acetate 

 thus formed (Ibid. 16, 1718). 



NOTE : The identity of the natural and syn- 

 thetical products requires confirmation. 



