158 



AROMATIC ALCOHOLS AND PHENOLS [81-83 A. 



from Myrcia (Eugenia) acris, W. 

 Indies (Mittmann, Arch. Pharm. 227, 



Occurs also in the oil from the 

 ( clove bark ' of Amboyna from Cinna- 

 momum culilawan (Gildemeister and 

 Stephan, Arch. Pharm. 235, 582), and 

 in certain oils of lemon poor in gera- 

 niol (Schimmel's Ber. Oct. 1898; 

 Ch. Centr. 1898, 2, 985). Methyleu- 

 genol probably occurs in matico oil 

 from the leaves of Piper angustifolium 

 (Ibid.). 



The betelphenol or chavibetol of the 

 ethereal oil of Piper belle (Bertram and 

 Gildemeister, Journ. pr. Ch. [2] 39, 

 349) is possibly identical with this 

 methyleugenol. Occurs in Ceylon 

 ' Lana Batu ' and in Java citronella 

 oils (SchimmeFs Ber. Oct. 1899 ; Ch. 

 Centr. 1899, 2, 880 ; Journ. Soc. Ch. 

 Ind. 19, 556). 



Methyleugenol is a constituent of the 

 oil of Asarum arifolium (Miller, Arch. 

 Pharm. 240, 371 ; Ch. Centr. 1902, 

 2, 642). 



SYNTHETICAL PROCESS. 



[A.] From catechol [69], glycerol 

 [48], and methyl alcohol [13]. Catechol 

 is by methylation converted into vera- 

 trole (Behal and Choay, Bull. Soc. [3] 

 9, 142; Gorup, Ann. 147, 248; Mar- 

 asse, Ann. 152, 74). Glycerol is con- 

 verted into allyl iodide by distilling 

 with iodine and phosphorus (for refer- 

 ences see under isobutyl alcohol [18 ; 

 D]), and veratrole when heated with 

 allyl iodide and zinc gives methyl- 

 eugenol (Moureu, Comp. Rend. 121, 

 721). 



82. Thymoquiiiol ; 



Hydrothymoquinone ; 



1 : 4-Methylmetlioethyl-2 : 5- 



Phenediol. 



CH, 



NATURAL SOURCES. 



In oil of wild bergamot from Monarda 

 fstulosa (Brandel and Kremers, Pharm. 

 Rev. 19, 200 ; 244), and probably in 

 Algerian oil of bitter fennel (Tardy, 

 Bull. Soc. [3] 27, 994). 



SYNTHETICAL PROCESSES. 



[A.] From thymol [67] through 

 thymoquinone and reduction of latter 

 (see below under the dimethyl ether 

 [83; A]). 



[B.] From carvacrol [66] through 

 thymoquinone, &c. [83; B]. 



83. Dimethylthymoquinol ; 



Thymoquinol Dimethyl Ether ; 



1 : 4-Methylmethoetliyl-2 ; 5- 



Phenediol Dimethyl Ether. 



CH, 



I I* 



CH 3 . 



CH 3 . CH . CH 3 



NATURAL SOURCE. 



Occurs with phloryl isobutyrate in oil 

 of arnica root from Arnica montana 

 (Sigel, Ann. 170, 363). 



SYNTHETICAL PROCESSES. 



[A.] Thymol and derivatives [67] on 

 oxidation give thymoquinone (Lalle- 

 mand, Jahresber. 1854, 592 ; Paternb, 

 Ber. 8, 440; Steiner, Ber. 11, 289; 

 Andresen, Journ. pr. Ch. [2] 23, 172; 

 Bayrac, Bull. Soc. [3] 7, 99; Arm- 

 strong, Ber. 10, 297 ; Liebermann and 

 Ilinski, Ber. 18, 3194), and this on 

 reduction gives thymoquinol (Carstan- 

 jen, Journ. pr. Ch. [2] 3, 54; Lalle- 

 mand, Comp. Rend. 37, 498; Ann. 

 101, 121). The dimethyl ether should 

 be obtainable by methylation, but the 

 identity of the natural product with 

 the synthetical ether remains to be 

 established. 



