70-B.J 



RESORCINOL 



143 



Gilbody, W.H. Perkin, junr., and Yates, 

 Trans. *Ch. Soc. 79, 



SYNTHETICAL PROCESSES. 



[A.] Benzene can be converted into 

 resorcinol by various processes : 



By nitration and partial reduction 

 m-dinitrobenzene and m-nitraniline can 

 be obtained (Deville, Ann. Chim. [3] 3, 

 187 ; Muspratt and Hofmann, Ann. 57, 

 214; Beilstein and Kurbatoff, Ann. 176, 

 43 ; Anschiitz and Heusler, Ber. 19, 2 1 6 1 ; 

 Wiilfing, Germ. Pat. 67018 of 1891; 

 Ber. 26, Ref. 421). The latter gives m- 

 iodonitrobenzene by the diazo-method 

 (Griess, Zeit. [2] 2, 218), m-iodaniline 

 by reduction (Ibid.), and m-iodophenol 

 by the diazo-method (Noelting and 

 Strieker, Ber. 20, 3020). The latter on 

 fusion with potash gives resorcinol 

 (Korner, Zeit. [2] 4, 322). 



Or m-nitraniline can be converted 

 into m-nitrophenol by the diazo-method 

 (Fittig and Bantlin, Ber. 7, 179; 11, 

 2099 ; Henriques, Ann. 215, 323 ; 

 Wagner, Journ. pr. Ch. [2] 32, 70), 

 m-aminophenol by reduction (Bantlin, 

 Ber. 11, 2101), and resorcinol by the 

 diazo-method (Ibid.). 



Or m-dinitrobenzene can be reduced to 

 m-phenylenediamine, which, on heating 

 with dilute acids to a high temperature, 

 is converted (partially) into resorcinol 

 (Meyer, Ber. 30, 2569). 



Metadinitrobenzene when boiled with 

 potassium cyanide and methyl alco- 

 hol is converted into the nitrile of 6- 

 nitro-2-methoxybenzoic acid (Lobry de 

 Bruyn, Rec. Tr. Ch. 2, 212). The 

 latter on heating with methyl alcohol 

 and potash is converted into the nitrile 

 of 2 : 6-dimethoxybenzoic acid (Ibid. 

 219), which, on heating with strong 

 hydrochloric acid at 170, splits up into 

 carbon dioxide, methyl chloride, am- 

 monium chloride, and resorcinol. Or 

 by potash fusion the nitrile is converted 

 into 2 : 6-dihydroxybenzoic acid, which 

 splits up into carbon dioxide and resor- 

 cinol on heating above 167. 



Or benzene may be nitrated, the mono- 

 nitrobenzene converted into m-nitro- 

 sulphonic acid by fuming sulphuric 

 acid (Limpricht and Bernthsen, Ann. 



177, 82), into m-sulphanilic acid by 

 reduction, and m-aminophenol by fusing 

 the latter with caustic soda (Gesell. f. 

 Ch. Ind., Germ. Pat. 44792 of 1888; 

 Meyer and Sundmacher, Ber. 32, 2112). 



Benzene when sulphonated under 

 appropriate conditions gives p- and m- 

 disulphonic acids, the proportions vary- 

 ing according to the conditions of 

 sulphonation (Buckton and Hofmann, 

 Journ. Ch. Soc. 9, 255 ; Barth and 

 Senhofer, Ber. 8, 754 ; 1477 > Q ) 9^9 > 

 Egli, Ber. 8, 817 ; Limpricht, Ber. 

 9, 550; Korner and Monselise, Ibid. 

 583 ; Binschedler and Busch, Monit. 

 Sci. 1878, 1169). Both p- and m- 

 benzenedisulphonic acid (the former by 

 isomeric transformation) give resorcinol 

 on fusion with caustic alkali, this being 

 the technical process (Garrick, Zeit. 

 [2] 5, 551 ; Barth and Senhofer, Ber. 8, 

 1483 ; Degener, Journ. pr. Ch. [2] 2O, 

 319 ; Genvresse, Bull. Soc. [3] 15, 409 ; 

 Fahlberg, Am. Ch. Journ. 2, 195 ; Bin- 

 schedler and Busch, Jahresber. 1878, 

 1137 and 1184; Schoop, Zeit. ch. 

 Ind. 1887, II, I; Miihlhiiuser, Ding. 

 Poly. Journ. 263, 154 ; Journ. Soc. Ch. 

 Ind. 6, 284). 



[B.] From toluene (see under benzyl 

 alcohol [54 ; A, &c.]) through p-nitro- 

 toluene by nitration, 4-nitrotoluene-2- 

 sul phonic acid by sulphonation (Beilstein 

 and Kuhlberg, Ann. 155, 8 ; Jenssen, 

 Ann. 172, 230), the amino-acid by reduc- 

 tion (B. and K. Ann. 172, 230 ; Jenssen, 

 loc. cit. 233 ; Brackett and Hayes, Am. 

 Ch. Journ. 9, 400), p-cresol-2-sulphonic 

 acid by the diazo-method (Jenssen, loc. 

 cit. 237), and 2 : 4-dihydroxybenzoic 

 (2 : 4-phenediolcarboxylic or/3-resorcylic) 

 acid by potash fusion of the cresolsul- 

 phonic acid (Ascher, Ann. 161, n). 

 /3-Resorcylic acid on heating with sodium 

 hydroxide, or per se, gives resorcinol 

 (Senhofer, Ber. 12, 1259). 



Or toluene may be converted into the 

 2 : 4-disulphonic acid by sulphonation 

 (Hakanson, Ber. 5, 1085 ; Gnehm and 

 Forrer, Ber. 10, 542 ; Gnehm, ibid. 

 1276 ; Fahlberg, Ber. 12, 1052; Klason 

 and Berg, Ber. 13, 1 1 70; Senhofer, Ann. 

 164, 1 26 ; Klason, Ber. 19, 2890), the 

 disulphonic acid oxidised to 2 : 4-di- 

 sulphobenzoic acid (Blomstrand, Ber. 5, 



