152 



AROMATIC ALCOHOLS AND PHENOLS [72 B-75. 



o-cresol can be converted into tolu- 

 quinone-oxime (nitroso-o-cresol) by 

 nitrosylsulphate (Noelting and Kohn, 

 Ber. 17, 370), and this gives 5-amino- 

 cresol on reduction (Ibid.}. 



73. Quiiiol Methyl Ether ; 

 p-Hydroxyanisole ; 

 p-Methoxyphenol. 



HO 



NATURAL SOURCE. 



Occurs with the glucoside of quinol 

 (arbutin) as the glucoside methylarbutin 

 [159] (see under quinol [7l] for botanical 

 sources). 



SYNTHETICAL PROCESS. 



[A.] From quinol [71] and methyl 

 alcohol [13] by heating the potassium 

 compound of the former with potassium 

 methyl sulphate (Hlasiwetz and Haber- 

 mann, Ann. 177, 338), or by heating 

 the potassium compound with methyl 

 iodide diluted with methyl alcohol 

 (Hesse, Ann. 20O, 354). 



74. Quinol Ethyl Ether; p-Hydroxy- 



phenetole ; p-Ethoxyplieiiol. 



HO 



O.C.H 5 



NATURAL SOURCES. 



Occurs in small quantity in oil of 

 star-anise from Itticium veritm (Oswald 

 in Beilstein's ' Handb. d. org. Chem.' 

 3rd ed. II, 939) ; in Chinese oil of star- 

 anise (Tardy, Bull. Soc. [3] 27, 990). 



SYNTHETICAL PROCESSES. 



[A.] From qidnol [7l] and alcohol [14] 

 by heating the potassium compound of 

 the former with ethyl iodide (Wichel- 

 haus, Ber. 12, 1501). 



[B.] From phenol [60] and alcohol 

 [14] through the ethyl ether, phenetole 

 (Cahours, Ann. 78, 226 ; Kolbe, Journ. 

 pr. Ch. [2] 27, 424), p-nitrophenetole 

 by nitration (Hallock, Am. Ch. Journ. 

 1, 271), phenetidine by reduction (Wag- 

 ner, Journ. pr. Ch. [2] 27, 206), and the 

 diazo-reaction with latter (Hantzsch, 

 Ibid. 22, 462). Or phenol can be 

 nitrated, the p-nitrophenol converted 

 into p-nitrophenetole by heating the 

 potassium salt with potassium ethyl 

 sulphate in alcohol (Willgerodt and 

 Ferko, Journ. pr. Ch. [2] 33, 153), and 

 then into phenetidine, &c v as before. 



[C.] From salicylic acid [Vol. II] and 

 alcohol [14] through ethyl salicylate 

 (Cahours, Ann. 52, 332; 74, 314; 

 Gottig, Ber. 9, 1473)- The latter, 

 according to Baly (Ann. 70, 269), gives 

 phenetole on distillation with baryta, 

 and this can be treated as under B. 



[D.] Benzene [6] can be converted 

 into p-nitrophenetole by boiling p-chlor- 

 nitrobenzene with alcoholic potash 

 (Willgerodt, Ber. 15, 1002), and this 

 can be converted as under B. 



75. Orcinol ; 3 : 5-Dihyclroxy toluene ; 

 Methylresorciiiol ; Methyl-3 : 5- 

 Pheuediol. 



CH S 



NATURAL SOURCES. 



Orcinol does not occur in the free 

 state in the vegetable kingdom, but the 

 complex is contained in certain acids 

 obtained from lichens. Roccella tinctoria, 

 R.fuciformis, and R. montagnei have long 

 been known to yield orcinol. The com- 

 plex exists in the following com- 

 pounds : 



Evernic acid from Evernia pmnastri, 

 var. vulgaris, Ramalina pollinaria (Sten- 

 house, Ann. 68, 84 ; 155, 55 ; Hesse, 

 Ann. 117, 297 ; Journ. pr. Ch. [2] 57, 

 250 ; Zopf, Ann. 297, 300 ; 306), and 

 Physcia ( = Anaptyckid) ciliaris (Hesse, 

 Journ. pr. Ch. [2] 58, 465). 



