35 B-36 A.] 



2-6-DIMETHYL-.2-HEPTENOL-6 



magnesium methiodicle on the ketone 

 (in ethereal solution) and decomposition 

 of the magnesium compound by acid 

 (Barbier, Comp. Rend. 128, no ; Sand 

 and Singer, Ber. 35, 3183). 



NOTE : The dimethylheptenol obtained by 

 th is method is (CH 3 ) a : C : CH . [CH 2 1 2 . C(CH 3 ) a . 

 OH. 



36. Geraniol ; Lemonol ; 

 2 : 6-Dimethyl-2 : 6-Octadienol-8. 



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



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



NATURAL SOURCES. 



In East Indian geranium or palma- 

 rosa oil from Andropogon schcenanthus 

 (Jacobsen, Ann. 157, 232); in oil of 

 citronella from Andropogon nardus, Pun- 

 jaub, Ceylon, Singapore, &c. (Schim- 

 mel's Ber. Oct. 1893) ; in African, 

 Spanish, French, and Reunion geranium 

 oils from Pelargonium odoratissimum, 

 P. capitatiim, P. radula, &c. (Gintl, 

 Jahresber. 1879, 942 ; Bertram and 

 Gildemeister, Journ. pr. Ch. [2] 49, 

 191 ; Tiemann and Schmidt, Ber. 29, 

 924) ; and in German and Turkish oils 

 of rose from Rosa damascena, R. alba, 

 &c. (Bertram and Gildemeister, foe. 

 cit. : see also Eckart, Ber. 24, 4205 ; 

 Arch. Pharm. 229, 355; Barbier, 

 Comp. Rend. 117, 177 ; Bull. Soc. [3] 

 9, 999). _ 



Geraniol occurs in ylang-ylang oil 

 from Cananga odorata (Reychler, Bull. 

 Soc. [3] 11, 407; 576; 1045; 13, 

 140) ; in French oil of lavender from 

 Lavandula sp. (Schimmel's Ber. April, 

 1898) ; in oil of neroli from the flowers 

 of the bitter orange, Citrus bigaradia, 

 and in the ( orange-flower water ' (Tie- 

 mann and Semmler, Ber. 26, 2711 ; 

 Hesse and Zeitschel, Journ. pr. Ch. [2] 

 64, 245) ; in petit-grain oil from 'the 

 leaves, shoots, and fruit of the same 

 plant (Passy, Bull. Soc. [3] 17, 519; 

 Charabot and Pillet, Ibid. 21, 74) ; in 

 petit-grain oil from Paraguay (Schim- 

 mel's Ber. Oct. 1902; Ch. Centr. 1902, 

 2, 1 208) ; in lemon-grass oil from the 

 Indian Andropogon citratus (SchimmeFs 

 Ber. Oct. 1894; also Oct. 1898; Ch. 



Centr. 1898, 2, 985: compare Stiehl, 

 Journ. pr. Ch. [2] 58, 51 ; Tiemann, 

 Ber. 32, 835; Labbe, Bull. Soc. [3] 

 21, 77); and in oil of linaloe from the 

 wood of the Mexican Bursera delpe- 

 c/iiana or J3. aloeorylon (SchimmeVs Ber. 

 April, 1892; Oct. 1894; Oct. 1900). 



Occurs also in oil of sassafras leaves 

 (Power and Kleber, Pharm. Rev. 14, 

 103; Ch. Centr. 1897, 2, 42); in oil 

 of balm mint from Melissa officinalis 

 (Flatau and Labbe", Comp. Rend. 126, 

 1725; Bull. Soc. [3] 19, 636); in 

 lemon oil from Citrus limomtm, Messina 

 and Palermo (Umney and Swinton, 

 Pharm. Journ. 61, 196; 370), and in 

 the oil from the leaves of Verbena tri- 

 phylla, Grasse (Theulier, Rev. gen. de 

 Chim. 6, 324; Ch. Centr. 1902, 2, 

 1208). 



The oil from Darwinia fascicularis of 

 Port Jackson contains geraniol and 

 60-65 per cent, of geranyl acetate 

 (Baker and Smith, Journ. and Proc. Roy. 

 Soc. of N. S. Wales, 33, 163; Journ. 

 Soc. Ch. Ind. 19, 848). Certain citron- 

 ella oils ( Javan and Cingalese ' Lana- 

 Batu') contain 32-38 per cent, geraniol 

 (Schimmel's Ber. Oct. 1899; Journ. 

 Soc. Ch. Ind. 19, 556). 



The oil from the leaves and twigs of 

 Eucalyptus macartkuri contains 60 per 

 cent, of geranyl acetate (Smith, Ch. 

 News, 83, 5). Geraniol is probably 

 contained in the oil of Eucalyptus 

 patentinervis (Schimmel's Ber. April, 

 1901 ; Ch. Centr. 1901, 1, 1007). The 

 oil from the rhizome of Asarum cana- 

 flense contains geraniol (Power, Pharm. 

 Rund. 6, 101 ; Power and Lees, Proc. 

 Ch. Soc. 17, 210 ; Trans. 81, 66). 



NOTE : The geraniol is contained in the above 

 oils sometimes free, sometimes combined as an 

 ester, and in some cases both free and com- 

 bined. The acid most frequently combined 

 with geranyl is acetic, but other acids, such as 

 tiglic, valeric, &c., are sometimes present. 

 Suggestions concerning the origin of geraniol 

 andalliedalcohols in plants have beenadvanced 

 by Charabot (Ann. Chim. [7] 21, 207, &c.). 



SYNTHETICAL PROCESSES. 



[A.] From citral [104] by reduction 

 in alcoholic solution with sodium 

 amalgam and acetic acid (Tiemann, 

 Ber. 31, 828). 



