141 A-143 B.] 



LUTEOLIN 



235 



are condensed by treatment with sodium 

 so as to form 2 : 4 : 6 : 3 1 : 4 : -penta- 

 methoxybenzoylacetophenone. The 



latter gives luteolin on heating with 

 strong- aqueous hydriodic acid (Kosta- 

 necki, Rdzycki, and Tambor, Ber. 33, 

 3415 ; Diller and Kostanecki, Ber. 34, 

 1449). 



142. Quinone ; Faradioxybenzene. 



NATURAL SOUKCES. 



Quinone appears to be among* the 

 products of the fermentation of grass, 

 and is probably the result of oxidation 

 by Bacteria (Emmerling, Ber. 30, 

 1870). 



Quinone is formed in albumin (pep- 

 tone) cultures by Streptotkrix chromo- 

 gena, Gasperini (Beyerinck, Centr. 

 Bakter. II, 6, I ; Ch. Centr. 1900, 1, 

 429 : see also Furuta, Ch. Centr. 1902, 



2, 35). 



The skin secretion of the Millipede, 

 Tuliis t^restris, possibly contains quinone 

 (Behal and Phisalix, Comp. Rend. 131, 

 1004). 



SYNTHETICAL PROCESSES. 



[A.] From quinol [7l] by oxidation 

 (Wohler, Ann. 51, 152 ; Nietzki, Ber. 

 19, 1468; Clark, Am. Ch. Journ. 14, 



555)- 



[B.] ^vom phenol [60] by oxidation 

 of the p-sulphonic acid (Schrader, Ber. 

 8, 760) ; or through p-nitro- and p- 

 aminophenol, and oxidation of the latter 

 (Schmitt and Siepermann, Journ. pr. 

 Ch. [2] 19, 317). 



[C.] From furfural [126] and acetone 

 [106] through pyromucic and muco- 

 bromic acids, nitromalonic aldehyde, 

 and p-nitrophenol (see und-e'r phloro- 

 glucinol [86 ; I] and resorcinol [70 ; 

 H]). 



[D.] From benzene [6; I, &c.] by the 

 oxidation of many derivatives with 

 open p-position or with easily removed 

 substituents in this position : 



From aniline (Hofmann, Jahresber. 

 1863, 415; Nietzki, Ber. 1O, 1934; 

 2005; 11, 1004; 19, 1467; Ann. 215, 

 125; Seyda, Ber. 16, 687; Schniter, 

 Ber. 20, 2283) by sodium dichromate 

 and sulphuric acid or other oxidising 

 agents. Also by the oxidation of 

 sulphanilic = aniline-p-sulphonic acid 

 (Meyer and Ador, Ann. 15 9, 7 ; Schrader, 

 Ber. 8, 760). 



Or from benzene (or aniline) through 

 p-phenylenediamine and oxidation of 

 the latter (Hofmann, loc. cit. 422). 

 Or directly from benzene by combina- 

 tion with chromium oxychloride and 

 decomposition of the product with 

 water (Etard, Ann. Chim. [5] 22, 

 270). 



The oxidation of aniline by chromic 

 acid mixture is facilitated by electro- 

 lytic action (Darmstadter, Germ. Pat. 

 109012 of 1897; Ch. Centr. 1900, 2, 

 151 : for electrolytic oxidation in sul- 

 phuric acid of benzene to quinone see 

 Kempf, Germ. Pat. 117251 of 1899; 

 Ch. Centr. 1901, 1, 348). 



143. Thymoquinone. 



CH 3 



NATURAL SOURCE. 



Occurs in wild bergamot oil from 

 Monardafistulosa (Brandel and Kremers, 

 Pharm. Rev. 19, 200; 244). 



SYNTHETICAL PROCESSES. 



[A.] From thymol [67] by oxidation 

 (see under thymoquinol dimethyl ether 

 [83; A]). 



[B.] From carvacrol [66] by oxida- 

 tion (83; B). 



