78-81.] 



MESORCINOL 



157 



linic acids. The latter may be a mesor- 

 cinol derivative (Hesse, Journ. pr. Ch. 

 [2] 62, 447). 



SYNTHETICAL PROCESS. 



[A.] From me-ntylene (see under 

 benzyl alcohol [54 ; D ; E ; P ; G- ; H, 

 &c.]), which on nitration gives a dinitro- 

 derivative, and this by mild reduction 

 nitromesidine (Fittig, Ann. 141, 133; 

 Maule, Ann. 71, 137 ; Knecht, Ann. 

 215, 98 -, Klobbie, Rec. Tr. Ch. 6, 33 ; 

 Kiister and Stallberg, Ann. 278, 214). 

 Nitromesidine gives by the diazo- 

 method nitromesitol, and the latter 

 aminomesitol by reduction (Knecht, loc. 

 cit.}. Aminomesitol by the diazo-method 

 gives mesorcinol (Knecht, Ann. 215, 100). 



NOTE : For production of nitromesidine 

 from mononitromesitylene and mesidine see 

 papers by Fittig, Ann. 141, 132 ; Fittig and 

 Storer. Ann. 147, 2 ; Schultz, Ber. 17, 477 ; 

 Ladenburg, Ann. 179, 165 ; Biedermann and 

 Ledoux, Ber. 8, 58 ; Noelting and Stoeckling, 

 Ber. 24, 570). 



79. Isoeugenol; 



1 '-Prop eiiy 1-3 : 4-PheiiecTiol 3-Metliyl 

 Ether. 



CH:CH.CH 3 



HO 



NATURAL SOURCE. 



In ylang-ylang oil (Schimmers Ber. 

 Oct. 1901 Ch. Centr. 1901, 2, 1007). 



SYNTHETICAL PROCESS. 



[A.] From vanillin [l2l] and pro- 

 pionic acid [Vol. II]. vanillin is con- 

 verted into propionylhomoferulaic acid 

 by heating with propionic anhydride 

 and sodium propionate (Tiemann and 

 Kraaz, Ber. 15, 3060). Homoferulaic 

 acid obtained from the propionyl com- 

 pound by hydrolysis gives isoeugenol 

 on heating with lime (Ibid. 2063). Or 

 from vanillin and ethyl alcohol [14] by 

 the interaction of the aldehyde and 

 magnesium ethiodide (Behal and Tiffe- 

 neau, Comp. Rend. 132, 563). 



8O. Methylisoeugeiiol ; 



Isoeugenol Methyl Ether ; 



1 '-Prop eiiy 1-3 : 4-Plieuediol 



Dimethyl Ether. 



CH : CH . CH, 



NATURAL SOURCE. 



A constituent of the oil of Asarum 

 arifolium (Miller, Arch. Pharm. 24O, 

 371 i Ch. Centr. 1902, 2, 642). 



SYNTHETICAL PROCESS. 



[A.] From isoeugenol [79] and methyl 

 alcohol [13] by methylation of the 

 phenol with methyl iodide and alcoholic 

 potash (Ciamician and Silber, Ber. 23, 

 1164). 



NOTE : The synthetical product was obtained 

 from eugenol, but this undergoes isomeric trans- 

 formation into isoeugenol under the influence 

 of the alcoholic potash. 



81. Methyleugeiiol ; 



3 : 4-Dimethoxyallylljenzeiie ; 



1 '-Prop eny 1-3 : 4-Plieiiediol Dimethyl 



Ether. 



CH 2 . CH : CH., 



OCH a 



OCH, 



NATURAL SOURCES. 



In oil of paracoto bark, Bolivia 

 (Wallach and Rheindorff, Ann. 271, 

 300) ; in oil from the root of Asarum 

 europaum (Petersen, Arch. Pharm. 226, 

 89 ; Ber. 21, 1057 : compare Mittmann, 

 Arch. Pharm. 227, 543, who suggests 

 methylisoeugenol), and A. canadense 

 (Power, Pharm. Rund. 6, 101 Proc. 

 Am. Pharm. Assoc. 28, 464 ; Power 

 and Lees, Proc. Ch. Soc. 17, 2io; 

 Trans. 81, 67). Also in oil of bay 



