96 III Q-100.] 



HEXOIC ALDEHYDE 



189 



propylene glycol on reduction with 

 sodium amalgam. From the glycol 

 through propanal, &c., as above 

 under A. 



97. Heptoic Aldehyde ; (Enanthol ; 

 Heptanal. 



CH 3 .CH 2 .CH 2 .CH 2 .CH 2 .CH 2 .CHO 



NATURAL SOURCES. 



(Enanthic aldehyde occurs in rancid 

 olive oil ; probably a bacterial product 

 derived from olei'c acid (Scala, Ch. 

 Centr. 1898, 1, 439; from Staz. sper. 

 agrar. 30, 613). This aldehyde occurs 

 also in rancid fat (Nagel, Am. Ch. 

 Journ. 23, 172). 



SYNTHETICAL PROCESS. 



[A.] Sebacic acid [Vol. II] gives 

 cenanthol, among other products, when 

 heated with lime (Calvi, Ann. 91, no; 

 Petersen, Ann. 103, 184 : see also Dale 

 and Schorlemmer, Ann. 199, 149). 



98. Octoic Aldehyde ; Octanal. 

 C 7 H 15 .CHO 



NATURAL SOURCE. 



This aldehyde possibly occurs in oil 

 of lemon (v. Soden and Rojahn, Ber. 

 34, 3809). 



SYNTHETICAL PROCESSES. 



[A.] Prom n-octyl alcohol [28] by 

 oxidation (Schimmel's Ber. April, 1899 ; 

 Ch. Centr. 1899, 1, 1043). 



[B.] From butyric aldeJiyde [94] 

 through a-ethyl-/3-propylacrolein = oc- 

 tenoic aldehyde, by the action of dilute 

 caustic alkali (Raupenstrauch, Monats. 

 8, 112). The acrolein reduces, by iron 

 arid acetic acid, to a secondary octanal, 

 which is ethylbutylacetaldehyde (Ibid. 



115). 



[C.] (Enanthol [97] and nitrometJiane 

 (see under hydrogen cyanide [172 ; J 

 and Y]) condense under the influence of 



alkali or sodium to form nitro-octanal, 

 which, on heating with zinc chloride, 

 gives nitro-octylene. The latter, by 

 reduction with zinc and acetic acid, 

 yields the oxime of octanal, from which 

 the aldehyde can be obtained by hydro- 

 lysis (Bouveault and Wahl, Comp. 

 Rend. 134, 1226). 



[D.] From octoic and formic acids 

 [Vol. II] by distilling a mixture of the 

 calcium salts (Schimmel & Co., Germ. 

 Pat. 126736 of 1900 ; Ch. Centr. 1901, 

 2, 1375)- 



NOTE : An octoic aldehyde is said to occur 

 among the products of distillation of castor-oil 

 soap (Limpricht, Ann. 93, 242 ; Bouis, Ann. 

 China. [3] 48, 99 ; Stadeler, Journ. pr. Ch. 72, 

 241 ; Dachauer, Ann. 106, 270 ; Be"hal, Bull. 

 Soc. [2] 47, 33 ; 163). 



The constitution of the natural aldehyde has 

 not been determined. 



99. Ennoic or Nonoic Aldehyde ; 

 Nonanal. 



C 8 H 17 .CHO 



NATURAL SOURCES. 



Occurs in oil of lemon (v. Soden and 

 Rojahn, Ber. 34, 2809), in oil of 

 mandarin orange (Schimmel's Ber. Oct. 

 1901; Ch. Centr. 1901,2, 1007), and 

 in Ceylon oil of cinnamon (SchimmeFs 

 Ber. April, 1902; Walbaum and 

 Hiithig, Journ. pr. Ch. [2] 66, 47). 



SYNTHETICAL PROCESS. 



[A.] From nonoic and formic acids 

 [Vol. II] by distilling a mixture of the 

 calcium salts (Schimmel & Co., Germ. 

 Pat. 126736 of 1900 ; Ch. Centr. 1901, 

 2, 1375). 



NOTE : The constitution of the natural alde- 

 hyde has not yet been determined. 



100. Decoic Aldehyde ; Decanal. 

 CH 3 [CH 2 ] 8 .CHO 



NATURAL SOURCES. 



According to Schimmel & Co. 

 (SchimmeFs Ber. Oct. 1900) the oil of 

 sweet orange contains n-decoic aldehyde 



