67 B-69.] 



THYMOL 



137 



tion with zinc dust and hydrochloric 

 acid followed by sodium in alcoholic 

 solution (v. Baeyer and Seuffert, Ber. 

 34, 47). 



[C.] Cymene [6] is brominated and 

 then sulphonated. The bromsulphonic 

 acid on heating- with ammonia and zinc 

 dust is debrominated, and the 3-cymene- 

 sulphonic acid thus obtained gives 

 thymol on fusion with alkali (Dines- 

 mann, Germ. Pat. 125097 of 1900; 

 Ch. Centr. 1901, 2, 1030; Eng. Pat. 

 J 3745 of 1901; Journ. Soc. Ch. Ind. 

 20, 1019). 



68. Anethole ; Anisstearoptene ; 



Fara-auol Methyl Ether ; 



! 1 -Propenyl-4-Anisole. 



CH : CH . CH, 



OCH 3 



NATURAL SOUHCES. 



In oil of aniseed from Pimpinella 

 anisum (De Saussure, Ann. Chim. [2] 

 13, 280 ; Dumas, Ann. 6, 245 ; Blan- 

 chet and Sell, Ibid. 287 ; Cahours, 

 Ibirl. 41, 56; 56, 177; Laurent, Ibid. 

 44, 313 ; Gerhard t, Ibid. 318 ; 48, 234 ; 

 Journ. pr. Ch. [i] 36, 267), and in oil of 

 star-anise from lUiclum verum (Cahours, 

 Comp. Rend. 12, 1213; Ann. 35, 313; 

 Persoz, Comp. Rend. 13, 433 ; Ann. 44, 

 311); in Chinese oil of star-anise (Tardy, 

 Bull. Soc. [3] 27, 990). 



In oil of anise-bark from a species of 

 Illicium (? parviflorum) from Madagas- 

 car (SchimmePs Ber. April, 1892); in 

 oil of fennel from Fceniculum vulgare 

 (Blanchet and Sell, Ann. 6, 287 ; 

 Cahours, Ann. 41, 74; Journ. pr. Ch. 

 24, 359); 



In oil of French, Algerian, and 

 Galician bitter fennel (Tardy, Bull. 

 Soc. [3] 17, 660 ; 27, 994); in oil of 

 Japanese fennel (SchimmeFs Ber. Oct. 

 1893; Umney, Pharm. Journ. 57, 91); 

 in oil of Macedonian fennel and of 

 Indian fennel from F. panmorium 

 (Umney, loc. cit. 58, 226). 



Anethole has been found in the 



ethereal oil of Piper pellalum (Surie, Ch. 

 Centr. 1899, 1, 883), and in oil of Os- 



morrhiza longistylts from N. America 

 (Eberhardt, Pharm. Rund. 5, 149). 



NOTE : The anethole which Gerhardt be- 

 lieved to exist in oil of tarragon from Artemisia 

 dracunculus (Comp. Rend. 19, 489) has since 

 been shown to be the isomeric methylchavi- 

 col = estragol (Schimmel's Ber. April, 1892 ; 

 Grimaux, Comp. Kend. 117, 1089 '> Hell and 

 Gaab, Ber. 29, 344). 



SYNTHETICAL PROCESSES. 



[A.] From anisic aldehyde [120] 

 through methylparapropiocoumaric acid 

 by heating the aldehyde with propionic 

 anhydride and dry sodium propionate, 

 and distilling the acid thus formed 

 (Perkin, Journ. Ch. Soc. 31, I, 411). 



Or the anisic aldehyde may be heated 

 with sodium propionate and propionic 

 anhydride at 200, when anethole is 

 directly formed (Moureu and Chauvet, 

 Comp. Rend. 124, 404 ; Moureu, Ann. 

 Chim. [7] 15, 135). 



Or from anisic aldehyde and ethyl al- 

 cohol [14]. The aldehyde and magne- 

 sium ethiodide condense to form ane- 

 thole and a polymeride (Behal and Tif- 

 feneau, Comp. Rend. 132, 563 : see 

 also Bougault, Bull. Soc. [3] 25, 1160). 

 [B.] Fromji/ienol [60], propionic acid 

 [Vol. II], and methyl alcohol [13]. Phe- 

 nol is converted into anisole (see under 

 anisic aldehyde [120; B]), and the latter 

 into p-propionylanisole by treatment 

 with propionyl chloride in presence of 

 aluminium chloride (Gattermann, Ber. 

 22, 1129; Klages, Ber. 35, 2262). 

 Propionylanisole reduces to a carbinol 

 [i-propylol-(i 1 )-4-methoxy benzene], of 

 which the acetate gives anethole on 

 boiling with pyridine (Klages, loc. cit.). 



69. Catechol ; Pyrocatechol ; 



Orthodihydroxybenzene ; 



1 : 2-Fhenediol. 



HO 



,OH 



NATURAL SOURCES. 



Said to have been found in various 

 parts of plants, especially in autumnal 



