88 



ALCOHOLS 



[36 B-37. 



[B.] Linalool [37] gives geraniol on 

 heating with acetic anhydride or with 

 sulphuric and acetic acids and hydro- 

 lysis of the acetate (Barbier, Comp. 

 Rend. 116, 1200; 117, 132; Bouchar- 

 dat, Comp. Rend. 116, 1253; Bertram 

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

 49, 192 ; Tiemann and Semmler, Ber. 

 26, 2714; Bertram, Germ. Pat. 80711 

 of 1893, Ber. 28, Ref. 582). 



NOTE : The product ' licarhodol ' obtained 

 by Barbier (Comp. Rend. 116, 1200) by heating 

 1-linaloOl with acetic anhydride and hydro- 

 lysis is said to be a mixture of geraniol and 

 d-terpineol (Stephan, Journ. pr. Ch. [a], 58, 

 109 : see also Barbier and L6ser, Bull. Soc. [3] 

 17, 59)- 



37. Linalool; Licareol. 



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



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



or 

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



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



NOTE : For references to constitution see 

 paper by Harries and Schauwecker, Ber. 34, 

 2981 ; also Barbier, Bull. Soc. [3] 25, 687 ; 828. 

 According to Barbier the first of these formulae 

 represents myrcenol. 



NATURAL SOURCES. 



1-Linalool is contained in oil of linaloe 

 from Guiana, probably from the wood 

 of Ocotea ca^^data (Morin, Comp. Rend. 

 92, 998; 94, 733; Ann. Chim. [5] 

 25, 427 ; Theulier, Rev. Gen. de Chim. 

 3, 262; Bull. Soc. [3] 26, 468; 

 SchimmePs Ber. April, 1901), and in 

 Mexican oil of linaloe (see above under 

 geraniol [36] : Semmler, Ber. 24, 207 ; 

 Barbier, Comp. Rend. 114, 674; 116, 

 883; 121, 168). 



Oil of neroli (see under geraniol) 

 contains 1-linalool (Tiemann and Semm- 

 ler, Ber. 26, 2711 ; Hesse and Zeitschel, 

 Journ. pr. Ch. [2] 64, 245) ; so also 

 does oil of bergamot from Citrus ber- 

 gamia (Semmler and Tiemann, Ber. 25, 

 1182; Bertram and Walbaum, Journ. 

 pr. Ch. [2] 45, 602 ; Charabot, Comp. 

 Rend. 129, 728 ; Fabris, Abst. in 

 Journ. Soc. Ch. Ind. 19, 772), man- 

 darin oil from Citrus madurensis (Schim- 

 mePs Ber. Oct. 1901), oil of limette 



from the fruit of the Italian Citrus 

 limetta (Gildemeister, Arch. Pharm. 

 233, 174), and oil of lemon from Citrus 

 limonum from Palermo (Umney and 

 Swinton, Pharm. Journ. 61, 196; 370). 



Oil of petit-grain (see under geraniol) 

 contains d- and 1-linalool (Semmler 

 and Tiemann, Ber. 25, 1 1 86 ; Chara- 

 bot and Fillet, Bull. Soc. [3] 21, 74 : 

 1-linalool in Paraguay petit-grain oil, 

 SchimmePs Ber. Oct. 1902 ; Ch. Centr. 

 1902, 2, 1208). 



1-Linalool is contained also in oil of 

 spike lavender from Lavandula spica 

 (Bouchardat and Voiry, Comp. Rend. 

 106, 551; Bouchardat, Ibid. 117, 53; 

 1094), in French lavender oil (Bertram 

 and Walbaum, Journ. pr. Ch. [2] 45, 

 590) ; in ylang-ylang oil (see under 

 geraniol ; Reychler, Bull. Soc. [3] 11, 

 407 ; 576 ; 1045 ; 13, 140) ; in oil of 

 Origanum smyrnaum from Smyrna 

 (Gildemeister, Arch. Pharm. 231, 182) ; 

 in oil of balm mint from Melissa 

 officinalis (see under geraniol) ; in 

 Russian oil of spearmint from Mentfia 

 viridis (SchimmePs Ber. April, 1898; 

 Ch. Centr. 1898, 1, 991); and in oil 

 of thyme from Thymus vulgaris (Labbe*, 

 Bull. Soc. [3] 19, 1009). 



Also in lemon-grass oil (see under 

 geraniol : Tiemann, Ber. 32, 835) ; in 

 oil of jasmine from the flowers of 

 Jasminum grandijlorum with linalyl 

 acetate (Hesse and Miiller, Ber. 32, 

 574; 765; Hesse, Ibid. 2619 : see also 

 Erdmann, Ber. 34, 2281, note) ; in 

 German oil of rose (Walbaum and 

 Stephan, Ber. 33, 2304) ; (trace) in 

 citronella oil (see under geraniol : 

 SchimmePs Ber. Oct. 1899; Ch. Centr. 

 1899, 2, 880) ; in oil of sassafras 

 leaves (Power and Kleber, Pharm. Rev. 

 14, 403; Ch. Centr. 1897, 2, 42); in 

 French oil of sweet basil from Ocymum 

 basilicum (Dupont and Guerlain, Comp. 

 Rend. 124, 300; Bull. Soc. [3] 19, 

 151); and probably in oil from Euca- 

 lyptus patentinervis (see under geraniol), 

 and in oil from the leaves of Darwinia 

 taxifolia (Baker and Smith : see under 

 geraniol and SchimmePs Ber. Oct. 

 1900; Ch. Centr. 1900, 2, 969). 



Linalyl acetate is possibly contained 

 in the oil from Salvia sclarea (Schim- 



