60 C-H.] 



PHENOL 



121 



water at 230-230, or with strong 1 hydro- 

 chloric or hydriodic acid, or with dilute 

 sulphuric acid at 140-150 (Graebe, 

 Ann. 139, 143). 



Methyl salicylate gives phenol when 

 heated with dry aniline (Tingle, Am. 

 Ch. Journ. 24, 45). 



[D.] Parahydroxybenzoic acid [Vol. II] 

 gives phenol when distilled with lime ; 

 also when heated per se, or by heating 

 with sodium hydroxide, or by the dry 

 distillation of the sodium salt at 240- 

 250 (Gerhardt, Rev. Scien. 10, 210; 

 Rosenthal, Zeit. [2] 5, 627 ; Klepl, 

 Journ. pr. Ch. [2] 28, 194; Earth and 

 Schreder, Ber. 12, 1257; Kupferberg, 

 Journ. pr. Ch. [2] 16,425; Goldschmiedt 

 and Herzig, Monats. 3, 132). Also 

 by heating in sealed tube with dilute 

 sulphuric acid (Klepl, Journ. pr. Ch. [2] 



25, 464). 



p-Methoxybenzoic = anisic acid [Vol. II] 

 gives phenol among the products of 

 the distillation of the calcium salt 

 (Goldschmiedt and Herzig, Monats. 

 3, 127). 



[E.] From benzoic acid [Vol. II] by 

 fusion with caustic potash (Earth and 

 Schreder, Monats. 3, 802). 



Also through metasulphobenzoic acid 

 by sulphonation (Mitscherlich, Pogg. 

 Ann. 31, 287; 32, 227; Offermann, 

 Ann. 28O, 5; Earth, Ann. 148, 33), 

 and m-hydroxybenzoic acid by fusion 

 of the sulpho-acid with caustic potash 

 (Earth, loc. cit. ; Remsen, Zeit. [2] 

 7, 8i; 199). Or from benzoic acid 

 through metachlorbenzoic acid by chlori- 

 nation (Scharling, Ann. 41, 49; 42, 

 268; Stenhouse, Phil. Mag. 27, 129; 

 Ann. 55, 10; Field, Ann. 65, 55; 

 Otto, Ann. 122, 157; Hiibner and 

 Weiss, Ber. 6, 175), and fusion of the 

 chloro-acid with caustic potash (Dembey, 

 Ann. 148, 222). 



Or from benzoic acid through the 

 metanitro-acid by nitration (Mulder, 

 Ann. 34, 297; Gerland, Ann. 91, 186; 

 Hiibner, Ann. 222, 72; Holleman, 

 Zeit. physik. Ch. 31, 79), m-amino-acid 

 by reduction (Zinin, Berz. Jahresber. 



26, 450; Journ. pr. Ch. 36, 103; 

 Gerland, Ann. 86, 143; 91, 188; 

 Schiff, Ann. 101, 94; Beilstein and 

 Wilbrand, Ann. 128, 265; Holleman, 



Rec. Tr. Ch. 21, 56), and m-hydroxy- 

 benzoic acid by the action of nitrous 

 acid (Gerland, Ann. 91, 189; Graebe 

 and Schultzen, Ann.' 142, 350). 



In all these cases the metahydroxy- 

 benzoic acid can be best converted into 

 phenol by heating the barium salt with 

 excess of baryta at 350 (Klepl, Journ. 

 pr. Ch. [2] 27, 159). 



[F.] Cinnamic acid [Vol. II] on treat- 

 ment with bleaching powder is said to 

 give metachlorbenzoic acid (Stenhouse, 

 Ann. 55, i), which can be converted 

 into m-hydroxybenzoic acid and phenol 

 as under E. 



Or cinnamic acid can be converted by 

 nitration into o- (with p^) nitrocinnamic 

 acid (Beilstein and Kuhlberg, Ann. 

 163, 126; Mu'ller, Ann. 212, 124), the 

 o-nitro-acid oxidised to o-nitrobenzoic 

 acid (B. and K. loc. cit. 134 ; Widn- 

 mann, Ber. 8, 393), reduced to anlhra- 

 nilic acid [Vol. II], the latter converted 

 into salicylic acid [Vol. II] by the 

 diazo-method, and then into phenol as 

 under C. 



Or cinnamic acid can be sulphonated, 

 the ortho- (? meta-) separated from the 

 parasulphonic acid, giving m-hydroxy- 

 benzoic acid on fusion with alkali (Rud- 

 neff, Ann. 173, 8). 



[G.] From gallic acid [Vol. II] by 

 heating the acid or its ester with strong 

 sulphuric acid so as to form rufigallic 

 acid =i : 2 : 3 : 5 : 6 : 7~hexahydroxy- 

 anthraquinone (Robiquet, Ann. 19, 

 204; Wagner, Jahresber. 1860, 288; 

 Ch. Centr. 1861, 47 ; Lowe, Journ. pr. 

 Ch. 107, 296; Zeit. [2] 6, 128; Jaffe", 

 Ber. 3, 694; Widman, Ber. 9, 856; 

 Klobukowski and Noelting, Eer. 8, 

 819; 9, 1256; 1O, 880). Rufigallic 

 acid on fusion with potash gives (with 

 m-hydroxybenzoic acid) 5-hydroxyiso- 

 phthalic acid (Schreder, Monats. 1, 

 437), and the latter on distillation 

 with lime gives phenol. Hydroxytere- 

 phthalic acid is also among the pro- 

 ducts of fused potash on rufigallic acid 

 (Ibid. 439), and this also gives phenol 

 on heating with sand. 



[H.] From benzoic aldehyde [114] 

 through the m-nitro-derivative by 

 nitration (Bertagnini, Ann. 79, 259 ; 

 86, 190; Lippmann and Hawliczek, 



