APPENDIX 



285 



with sodium in alcoholic solution (Bou- 

 veault and Blanc, Comp. Rend. 137, 

 328). 



60. Phenol (p. 119). 



Phenol is among- the products of the 

 decomposition of fodder bj micro- 

 organisms (Konig, Spieckermann, and 

 Olig ; Journ. Ch. Soc. 84, II, 447). 



To be added to synthetical pro- 

 cesses : 



[A, p. 1 20.] Haloid derivatives of 

 benzene, e. g. brombenzene, interact 

 with magnesium in ethereal solution 

 to form a phenyl-magnesium halide, 

 which is oxidised by air with the 

 formation of a product which yields 

 phenol (18 per cent.) on treatment with 

 aqueous alkali (Bodroux, Bull. Soc. [3] 

 31, 33)- 



[U, p. 124, note.] For preparation of gluta- 

 conic ester from acetonedicarboxylic acid via 

 /3-hydroxyglutaric acid see further Blaise, Bull. 

 Soc. [3] 29, 1012. 



61. Orthocresol (p. 124). 



To be added to synthetical pro- 

 cesses : 



[A, p. 124.] Also from toluene 

 through o-bromtoluene, o-bromtoluyl 

 magnesium bromide, and oxidation, &c., 

 of latter as under phenol (60 , A, above ; 

 Bodroux, loc. cit.). 



[J, p. 127.] Dihydrocarveol by oxida- 

 tion is converted into trihydroxyhexa- 

 hydrocymene, which by further oxida- 

 tion with sulphuric and chromic acids 

 gives i -methyl-4-ethylonecyclohexanol- 

 2, and this by the action of sodium 

 hypobromite yields i-methylcyclohexa- 

 nol-2-carboxylic-4-acid. By the action 

 of bromine at 190 the latter is con- 

 verted into 2-hydroxy-p-toluic acid 

 (Tiemann and Semmler, Ber. 28, 2144 : 

 see also Einhorn and Willstatter, Ann. 

 280, 88), which gives o-cresol as under 

 A, p. 125. 



[L, p. 128.] From camphor [175] 

 through cymene and then as under C, 

 p. 127. According to Renter (Ber. 16, 

 694), o-cresol is among the products 

 obtained by heating camphor with zinc 

 chloride. Pseudocumene is also among 



the products of decomposition of cam- 

 phor by this last process (Ibid.} and 

 possibly among the products obtained 

 by heating camphor with zinc dust 

 (Schrotter, Ber. 13, 1621). From 

 pseudocumene through m-xylene, &c., 

 as under B, p. 126. 



62. Metacresol (p. 128). 



To be added to synthetical pro- 

 cesses : 



[A, p. 129.] p-Xylene can be obtained 

 also from toluene or benzene by the 

 interaction of p-toluyl magnesium brom- 

 ide and dimethyl sulphate (Werner and 

 Zilkens, Ber. 36, 2116), or of p-brom- 

 phenyl magnesium bromide and di- 

 methyl sulphate in ethereal solution 

 (Houben, Ibid. 3083). 



[C, p. 129.] Or the ethyl ester of 

 m-hydroxyuvitic (= a-coccinic) acid is 

 decomposed on heating with the forma- 

 tion of 5-hydroxy-o-toluic acid (Claisen, 

 Ann. 297, 46). From the latter as 

 under A, p. 128. 



NOTE : m-Hydroxyuvitic ester has been ob- 

 tained also from ethoxymethylene-acetoacetic 

 ester (from acetoacetic and orthoformic ethyl 

 esters condensed by means of acetic anhydride, 

 Claisen, Ber. 26, 2731) and acetonedicarboxylic 

 ester (see under orcinol [75 ; C, p. 154]). The 

 two esters condense in presence of sodium 

 ethylate to form methylhydroxytrimesic tri- 

 ethyl ester, the sodium derivative of which is 

 converted into the diethyl ester on boiling with 

 water. jThe diethyl ester on distillation at 

 220-230 under 60 mm. pressure gives m- 

 hydroxyuvitic acid (Errera, Ber. 32, 2785 ; for 

 production of the ethyl ester of m-hydroxy- 

 uvitie acid from methenylbisacetoacetic ester 

 see further Claisen, Ann. 297, 43). 



[K, p. 130.] From camphor [175], 

 p-xylene being among the products 

 formed by heating this compound with 

 zinc dust (Schrotter, Ber. 13, 1621). 

 From p-xylene as under A, p. 129. 



63. Faracresol (p. 130). 



To be added to synthetical pro- 

 cesses : 



[A, p. 131.] Or from toluene through 

 p-bromtoluene, p-bromtoluyl magne- 

 sium bromide, and oxidation, &c., of 

 the latter as under phenol (60; A, 

 above in this appendix ; Bodroux, Bull, 

 Soc. [3] 31, 33). 



