86 



ALCOHOLS 



[32-35 B. 



32. Normal Primary Tetradecyl 

 Alcohol ; 1-Tetradecanol. 



NATURAL SOURCE. 



Occurs in small quantity as ester in 

 spermaceti [33] (Heintz, Ann. 84, 306 ; 

 92, 299 ; Hammarsten's ' Lehrb. d. 

 physiol. Chem/ 1895, p. 76). 



SYNTHETICAL PROCESS. 



[A.] From myristic acid [Vol. II] 

 through the aldehyde by distilling the 

 barium salt with barium formate (Krafft, 

 Ber. 13, 14 15), and reduction of the alde- 

 hyde with sodium in alcoholic solution 

 (Ibid. 16, 1720; 23, 2360). 



NOTE : The identity of the natural and syn- 

 thetical products requires confirmation. 



33. Cetyl Alcohol ; JGthal ; 1 Hexa- 

 decanol. 



CH 3 .[CHJ 14 .CH 2 .OH 



NATURAL SOURCES. 



As ester of palmitic acid in spermaceti 

 from the cranial cavity and blubber of 

 the sperm whale (Physetermacrocephalus), 

 from Delpfiinus tursio and D. edentulus. 

 Occurs also in oil from the dolphin 

 (DelpMnv* glo&icepg)and.w blubber of the 

 bottle-nose whale (Hyperoodon restrains 

 and H. bid ens). Cetyl acetate, laurate, 

 myristate, and stearate are present to a 

 small extent in some kinds of sperma- 

 ceti (Chevreul, ' Recherches sur les 

 Corps Gras/ p. 171; Ann. China. 7, 

 157 ; Dumas and Peligot, Ibid. [2] 62, 

 4; Dumas and Stas, Ibid. 73, 124; 

 Smith, Ibid. [3] 6, 40 ; Ann. 42, 247 ; 

 Berthelot and Pean, Ann. Chim. [3] 

 68, 413; Heintz, Ann. 84, 306; 92, 

 299; Pogg. Ann. 87, 21 ; 267; 92, 

 429; 588; Krafft, Ber. 17, 1627). 

 The alcohol is said to occur (as ester) in 

 the caudal glands of certain birds (ducks 

 and geese) (De Jonge, Zeit. physiol. Ch. 

 3, 225) ; also in the fat of ovarian 

 cysts (Ludwig, Zeit. physiol. Ch. 23, 

 38 ; v. Zeynek, Ibid. 48). 



SYNTHETICAL PROCESSES. 



[A.] From adipic acid [Vol. II] 

 through sebacic acid (see under n- 

 hexyl alcohol [23 ; E]) by distilling the 

 barium salt of the latter (Schorlemmer, 

 Proc. Roy. Soc. 19, 22; Ber. 3, 616). 



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

 through the aldehyde by distilling the 

 barium salt with barium formate (Krafft, 

 Ber. 13, 1416), reduction of the alde- 

 hyde with zinc dust and acetic acid, and 

 hydrolysis of the acetate thus formed 

 (Ibid. 16, 1721; 17, 1627). 



34. Octadecyl Alcohol ; 



1-Octadecanol. 



CH 3 .[CH 2 ] 16 .CH 2 .OH 



NATURAL SOURCE. 



An ester of this alcohol occurs in 

 spermaceti (Heintz, Ann. 84, 306 ; 92, 

 299; Krafft, Ber. 17, 1628). 



SYNTHETICAL PROCESS. 



[A.] From stearic and formic acids 

 [Vol. II] through stearic aldehyde 

 (Krafft, Ber. 13, 1417) and reduction 

 of the aldehyde in the usual way (Ibid. 

 16, 1722; 17, 1627). 



35. 2-6-Dimetliyl-2-Heptenol-6. 



(CH 3 ),:C:CH.CH 2 .CH 2 . 



C(CH 3 )(OH).CH 3 



NATURAL SOURCE. 



Said to occur in small quantity in oil 

 of linaloe (Barbier, Comp. Rend. 126, 

 1423)- 



SYNTHETICAL PROCESSES. 



[A.] From geraniol [36] by the action 

 of strong alcoholic potash at 150 

 (Barbier, loc. cit.}. 



NOTE : According to Tiemann (Ber. 31, 2991) 

 this product is methylheptenol corresponding 

 to methylheptenone. 



[B.] From methylheptenone [ill] and 

 methyl alcohol [13] by the action of 



