2-4.] 



NORMAL HEPTANE 



27 



2. Normal Heptane. 

 CH 3 .[CH 2 ] 5 .CH 3 



NATURAL SOURCE. 



Occurs in the exudation of the Cali- 

 fornian nut pine, Finns sabiniana 

 (Thorpe, Trans. Ch. Soc. 35, 296; 

 37, 213). Also in the resin of Pinus 

 jeffreyi (Blasdale, Journ. Am. Ch. Soc. 

 23, 163). 



SYNTHETICAL PROCESSES. 



[A.] From methyl and n-hexyl alcohols 

 [13 ; 23] by conversion into the corre- 

 sponding alkyl iodides and combination 

 of the alkyls by the action of sodium 

 on the iodides in ethereal solution 

 (general method of Wurtz, Ann. Chim. 

 [3] 44, 275 ; see also Frankland, Ann. 

 71, 171 j 74,41). 



[B.] From ethyl and n-amyl alcohols 

 [14 ; 20] as above. 



[C.] From n-propyl and n-butyl alco- 

 hols [15 ; 17] as above. 



[D.] (Enanthol [97] on reduction 

 with sodium amalgam or zinc dust and 

 acetic acid gives normal heptyl alcohol 

 (Bouis and Carlet, Ann. 124, 352; 

 Schorlemmer, Ann. 177, 303 ; Cross, 

 Ann. 189, 2; Jourdan, Ann. 200, 102 ; 

 Krafft, Ber. 16, 1723). The alcohol 

 gives n-heptyl iodide on heating with 

 aqueous hydriodic acid (Jourdan, loc. cit. 

 104), and this might be reduced to 

 n-heptane by the usual methods (see 

 under methane [l ; C]). 



Or oenanthol by the action of phos- 

 phorus pentachloride gives I : i-di- 

 chlorheptane = 03nanthylidene chloride 

 (Limpricht, Ann. 103, 81), which by 

 the action of alcoholic potash gives 

 6-(ct)-heptine = oenanthylidene (Ibid. ; 

 Rubien, Ann. 142, 294). The latter 

 combines with hydrogen by the ' con- 

 tact ' action of hot finely divided nickel 

 to form heptane (Sabatier and Sen- 

 derens, Comp. Rend. 135, 87). 



[E.] From azela'ic acid [Vol. II] 

 through heptane by heating the barium 

 salt with barium oxide (Dale, Journ. 

 Ch. Soc. 17, 258). 



[F.] From acetic and n-hepioic acids 



[Vol. II], a mixture of the potassium 

 salts giving a heptane on electrolysis 

 which is probably normal heptane 

 (Wurtz, Ann. 96, 372). 



NOTE : Many synthetical products belonging 

 to the aromatic series are said by Berthelot to 

 give heptane on heating to a high temperature 

 with strong aqueous hydriodic acid, but the 

 constitution of the heptanes thus obtained has 

 not beeil determined. (See for references under 

 methane [1 ; IJ and under isoheptyl alcohol 

 [27].) 



3. Normal Fentadecane. 

 CH 3 [CH 2 ] 13 . CH 3 



NATURAL SOURCE. 



Possibly a constituent of the essential 

 oil of Kaempferia galanga (P. van Rom- 

 burgh, Proc. K. Akad. Wetensch. 

 Amsterdam, 4, 618 ; Journ. Ch. Soc. 

 82, I, Abst. 633). 



SYNTHETICAL PROCESSES. 



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

 and methyl alcohol [13] by distilling 

 the barium salt of the acid in a vacuum 

 with sodium meth oxide (Mai, Ber. 22, 



2134). 



Or palmitic and acetic acids on dis- 

 tilling a mixture of the barium salts 

 give 2-heptadecanone (Krafft, Ber. 

 12, 1671), and this on oxidation with 

 chromic acid mixture gives pentadecylic 

 acid (Ibid.). The latter on heating 

 with hydriodic acid and phosphorus 

 to 240 gives n-pentadecane (Ibid. 15, 

 1700). 



4. Normal Heptacosane. 

 CH 3 [CH 2 ] 26 .CH 3 



NATURAL SOURCES. 



Occurs in beeswax (Schwalb, Ann. 

 235, 117) and in tobacco leaf (Thorpe 

 and Holmes, Trans. Ch. Soc. 79, 982 ; 

 see also Kissling, Ber. 16, 2432). 



