AROMATIC ALCOHOLS AND PHENOLS 



[71 F-0. 



13, 310; Fittica, Ber. 10, 1630). The 

 latter can be oxidised to o-nitrobenzoic 

 acid, and then treated as under C. 



Or from benzoic aldehyde through 

 toluene by heating- with strong hy- 

 driodic acid solution at 380 (Berthelot, 

 Jahresber. 1867, 346), o-nitrotoluene 

 by nitration (see under o-cresol [61; 

 A]), o-nitrobenzoic acid by oxidation 

 (Weith, Ber. 7, 1058; Widnmann, 

 Ann. 193, 225 ; Monnet, Reverdin, 

 and Noelting, Ber. 12, 443 ; Noyes, 

 Ber. 16, 53), and then as above. 



[G.] The er&toh [61; 62; 63] by 

 distillation with hot zinc dust (Baeyer, 

 Ann. 140, 295 ; Marasse, Ann. 152, 

 64), or by heating with phosphorus 

 trisulphide (Kekule and Fleischer, Ber. 

 6, 1088; Geuther, Ann. 221, 55), give 

 toluene, from which o-nitrobenzoic acid, 

 &c., can be obtained as above. 



[EL] Benzyl alcohol ,[54] heated with 

 hydriodic acid and phosphorus at 140 

 is reduced to toluene (Graebe, Ber. 8, 

 1 054), which can be treated as above. 



NOTE : All generators of toluene (see under 

 benzyl alcohol [54 ; A, &c.]) thus become 

 generators of quinol. 



[I.] Phenylacetic acid [Vol. II] when 

 nitrated gives the 2 : 4-dinitro-acid 

 (Radziszewski, Ber. 2, 210; Gabriel 

 and Meyer, Ber. 14, 823), and this by 

 reduction the 2-nitro-4-amino-acid {G, 

 and M. loc. cit. 824). The latter, on 

 replacing the NH 2 -group by hydrogen 

 by the diazo-method and the simul- 

 taneous action of nitrous acid, gives the 

 oxime of o-nitrobenzoic aldehyde (Ibid. 

 826 ; 15, 3057 ; 16, 520), from which 

 the nitro-aldehyde can be obtained by 

 oxidation with chromic acid mixture 

 (Ibid. 14, 829), and finally o-nitrobenzoic 

 acid by oxidation with potassium per- 

 manganate. Subsequent steps as above. 



Or the 2 : 4-dinitro-acid in alkaline 

 solution decomposes into 2 : 4-dinitro- 

 toluene (Radziszewski, Ber. 2, 210; 

 3, 648 ; Gabriel and Meyer, Ber. 14, 

 824), which on reduction with am- 

 monium sulphide gives 2-nitro-4-tolui- 

 dine (Beilstein and Kuhlberg, Ann. 155, 

 14). The latter by the diazo-method 

 yields o-nitrotoluene, from which o- 

 nitrobenzoic acid can be obtained by 

 oxidation (see above under F). 



[J.] Indigo [Vol. II] when boiled 

 with aqueous potash gives o-aminoben- 

 zoic (anthranilic] acid [Vol. II] (Fritz- 

 sche, Ann. 39, 83; Liebig, Ibid. 91), 

 which can be converted into quinol as 

 under D. 



[K.] Homogentisic acid [Vol. II] gives 

 quinol on fusion with potash. 



[L.] Gentisin [137] when fused with 

 potash gives 2 : 5-dihydroxybenzoic 

 (gentisic) acid (Hlasiwetz and Haber- 

 mann, Ann. 175, 62 ; 180, 345 ; Tie- 

 mann and Miiller, Ber. 14, 1988), which 

 can be converted into quinol as under B. 



[M.] Ettxanthone [136] gives quinol 

 among the products of fusion with 

 potash (Baeyer, Zeit. [2j 5, 569). 



[N.] Succinic acid [Vol. II] gives 

 quinol among other products by the dry 

 distillation of its salts (v. Richter, Journ. 

 pr. Ch. [2] 20, 207). 



Or succinic acid (ester) by the action 

 of sodium in presence of alcohol or of 

 dry sodium ethoxide can be converted 

 into succinylsuccinic (cyclohexanedione- 

 2 : 5-dicarboxylic- 1 : 4) ester (Fehling, 

 Ann. 49, 186 ; Herrmann, Ber. 10, 107 ; 

 Ann. 211, 306 ; Duisberg, Ber. 16, 133 ; 

 Volhard, Ibid. J 34 ; Piutti, Gazz. 20, 

 167; Vorlander, Ann. 28O, 186). The 

 latter on oxidation by air or bromine 

 gives p-dihydroxyterephthalic (quinol- 

 dicarboxylic or 2 : 5-phenedioldicarboxy- 

 lic) ester (Herrmann, loc. cit. 1 1 1 ; Ann. 

 211, 327), and the acid on dry distilla- 

 tion or on fusion with potash yields 

 quinol (Ibid. Ber. 10, 1 1 2 ; Ann. 211, 



33 6 )- 



Or succinylsuccinic ester can be con- 

 verted into dihydroxyterephthalic acid 

 by the action of phosphorus pentachloride 

 (Levy and Curchod, Ber. 22, 2108). 



Or from succinic acid through laevulic 

 acid (see under erythritol [50 ; C]) and 

 then through the dibromo-acid and di- 

 acetyl as below under O. 



[O.] From acetoacetic ester [Vol. II] 

 and its dibromo-derivative by brominff- 

 tion (Duisberg, Ann. 213, 143 ; Schb'n- 

 brodt, Ann. 253, 177 ; Epprecht, Ann. 

 278, 85). The latter when acted on in 

 dry ethereal solution by sodium gives 

 dihydroxyterephthalic ester (Wedel, 

 Ann. 219, 74). 



Or acetoacetic ester can be converted 



