37-38 B.] 



LINALOOL 



89 



meFs Ber. April, 1889; Oct. 1894). 

 1-Linalool is contained in Ceylon oil 

 of cinnamon (Ibid. April, 1902; Wal- 

 baum and Hiithig, Journ. pr. Ch. [2] 

 66, 47), and in oil of cinnamon leaf 

 (SchimmePs Ber. Oct. 1902 ; Ch. 

 Centr. 1902, 2, 1208). Linalool and 

 linalyl acetate are present in oil of 

 Gardenia (Parone, Boll. Ch. Farm. 41, 

 489; Ch. Centr. 1902, 2, 703). 



d-Linalool = coriandrol occurs in oil 

 of coriander from the fruit of Corian- 

 drum sativum (Kawalier, Ann. 84, 351 ; 

 Journ. pr. Ch. 58, 226 ; Grosser, Ber. 

 14, 2485; Semmler, Ber. 24, 306; 

 Barbier, Comp. Rend. 116, 1460) ; in 

 ' wartara ' oil from the fruit of Xantho- 

 xylon alatvm and X. acanthopodium 

 (SchimmePs Ber. April, 1900; Ch. 

 Centr. 1900, 1, 908); in oil of sweet 

 (Portugal) orange from the rind of the 

 fruit of Citrus aurantium (Parry, Ch. 

 Drug. 1900, pp. 462 and 722 ; Stephan, 

 Journ. pr. Ch. [2] 62, 523) ; in the 

 neroli oil from the flowers of the same 

 plant (Theulier, Bull. Soc. [3] 27, 278 : 

 a French neroli oil examined by Schim- 

 mel & Co. probably contained 1-lina- 

 lool ; Ch. Centr. 1902, 2, 1208), in 

 Chinese neroli oil from Citrus triptera 

 (Umney and Bennett, Pharm. Journ. 

 [4] 15, 146), and in oil of Asarum 

 canadense (Power and Lees, Proc. Ch. 

 Soc. 17, 2io ; Trans. 81, 63). 



Inactive linalool and linalyl isono- 

 noate are present in oil of hops (Chap- 

 man, Proc. Ch. Soc. 19, 72). 



NOTE : For remarks on general transforma- 

 tion and migration of linalool and other terpene 

 alcoholic compounds in plants, see papers by 

 Charabot, Bull. Soc. [3] 23, 189 ; Ann. Chim. 

 [7] 21, 207, &c. ; Charabot and Hebert, Comp. 

 Rend. 133, 390 ; Bull. Soc. [3] 25, 884 ; 955). 

 Linalool occurs in the above oils in some cases 

 in the free state and in other cases combined 

 as linalyl acetate, &c. 



SYNTHETICAL PKOCESS. 



[A.] Geraniol [36] by the action of 

 hydrochloric acid gives geranyl chloride 

 (Jacobsen, Ann. 157, 236), and this by 

 the action of alcoholic potash is con- 

 verted partially into inactive linalool 

 (Semmler and Tiemann, Ber. 31, 832). 

 A similar transformation is brought 

 about by heating geraniol with water 

 to 200 (Schimmel's Ber. April, 1898). 



Or sodium geranyl phthalate (from 

 geranyl chloride and phthalic acid [54 ; 

 B,]) gives i-linalob'l on steam distillation 

 of the neutral solution (Stephan, Journ. 

 pr. Ch. [2] 60, 244). 



NOTE: No method for resolving i-linaloftl 

 into its optical isomerides has yet been dis- 

 covered. 



38. Citronellol ; Bhodinol (?) ; 



2 : 6-Dimethyl-2-Octenol-8. 



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



CH(CH 3 ).CH 2 .CH 2 .OH 



NATURAL SOURCES. 



1-Citronellol occurs in Bulgarian and 

 German oil of rose and d- and 1-citron- 

 ellol in Spanish, African, and Reunion 

 oils of geranium from Pelargonium 

 odoratissimum, &c. (see under geraniol : 

 Hesse, Journ. pr. Ch. [2] 50, 478 ; 53, 

 238; Tiemann and Schmidt, Ber. 29, 

 922 ; Barbier and Bouveault, Comp. 

 Rend. 122, 737 ; Walbaum and Stephan, 

 Ber. 33, 2306 ; Schimmel's Ber. May, 

 1901 ; Journ. Soc. Ch. Ind. 20, p. 744)- 



Citronellol is also said to be contained 

 in Indian geranium (palmarosa) oil 

 (Flatau and Labbe, Comp. Rend. 126, 

 1725; Bull. Soc. [3] 19, 633 : compare 

 SchimmeFs Ber. Oct. 1898, p. 67). 

 Javan (but not Ceylon) oil of citronella 

 contains d-citronellol (SchimmeFs Ber. 

 April, 1902). 



SYNTHETICAL PROCESSES. 



[A.] From citronellal [105] by re- 

 duction with sodium amalgam and 

 acetic acid (Dodge, Am. Ch. Journ. 11, 

 463; Tiemann and Schmidt, Ber. 29, 

 906). 



NOTE : The aldehyde corresponding to the 

 above formula of Citronellol is probably not 

 identical with 1-citronellal but with the iso- 

 meric ' rhodinal ' of Bouveault (Bull. Soc. [3] 

 23,458 ; 463 : see also under citronellal [105]). 

 The above synthetical process may therefore 

 lead to the production of an alcohol isomeric 

 with the natural 1-citronellol (see also Harries 

 and Schauwecker, Ber. 34, 2981). 



[B.] From menthone [129] through 

 the oxime, nitrile, and aldehyde = men- 

 thocitronellal (Wallach, Ann. 277, 

 154; 278, 316; 296, 129). The latter 

 should be Bouveault's 'rhodinal,' and 



