116 



AROMATIC ALCOHOLS AND PHENOLS [54 Y-55. 



which on heating with phosphorus 

 pentoxide yields toluene among other 

 products (Wallach, Ann. 309, 7). 



Pulegone and mentJione [129] give 

 pyrotartaric acid among the products 

 of oxidation by potassium perman- 

 ganate (Markownikoff, Ber. 33, 1909). 

 Subsequent steps as above under N. 



[Z.] From malic acid [Vol. II] 

 through coumalic acid and crotonic 

 aldehyde [102], and then as above 

 under H. 



Malic acid also gives oxalacetic acid 

 on oxidation with hydrogen dioxide in 

 presence of ferrous salts. If the tem- 

 perature is not kept low pyroracemic 

 acid is produced (Fenton and Jones, 

 Trans. Ch. Soc. 77, 77). From oxal- 

 acetic acid through pyrotartaric acid, 

 &c., as before (see under n-propyl alcohol 

 [15; Z]). 



[AA.] From mannitol [5l], which 

 gives acrolein [lOl] among the pro- 

 ducts of oxidation by sulphuric acid 

 and manganese dioxide (Backhaus, 

 Jahresber. 1860, 522). Subsequent 

 steps via acrylic acid as under I, &c. 



[BB.] From alanine [Vol. II], which 

 gives acrylic acid on treatment with 

 methyl iodide in the presence of alkali 

 (Korner and Menozzi, Gazz. 11, 258 ; 



549 ; 13, 35)- 



[CO.] From oxalic and acetic acids 

 [Vol. II] and alcohol [14] through 

 aiethyloxalacetate and pyrotartaric 

 acid (see under n-propyl alcohol [15; 

 Z]). 



[DD.] From succinic acid [Vol. II] 

 through the dibromo-acid, ethoxyfuma- 

 ric acid, and oxalacetic acid (see under 

 n-propyl alcohol [15 ; Y]). From the 

 latter to pyrotartaric acid, &c., as under 

 n-propyl alcohol [15; Z]. 



[EE.] From fumaric or male'ic acid 

 [Vol. II] through dibromsuccinic acid 

 (n-propyl alcohol [15 ; EE]), and then 

 as above under DD. 



[PP.] From hydracrylic acid [Vol. II] 

 through acrylic acid (n-propyl alcohol 

 [15; S]). From acrylic acid through 

 a-chlorlactic acid, glyceric acid, &c., as 

 above under I, &c. 



[GG.] From isobutyl [18] or tertiary 

 butyl alcohol [19] through isobutylene 

 [18; A; 19; B]. Toluene is among 



the products formed by passing iso- 

 butylene through a hot tube (Noyes; 

 Beilstein, I, 115). 



NOTE : Generators of isobutylene thus become 

 generators of benzyl alcohol. 



[HH.] From lysine [Vol. II] through 

 pyrotartaric acid (see under n-propyl 

 alcohol [15 ; II]). 



[II.] From catechol [69] and hydrogen 

 cyanide [172] through dioxytartaric acid 

 and glyoxal (see under hydrogen cyanide 

 [172 ; P]), and the pyroracemic nitrile 

 and acid as above under H. 



[JJ.] From protocatechuic acid [Vol. 

 II] through dioxytartaric acid and 

 glyoxal, &c., as under hydrogen cyanide 

 [172 ; Q], and as above under H. 



55. Saligenin ; 

 Orthohydroxybenzyl Alcohol ; 



Plieuol-2-Methylol. 



CHo.OH 



NATURAL SOURCES. 



Occurs as the glucoside (salicin [157]) 

 in bark, twigs, and leaves of various 

 species of willow (Salix helix, S, pur- 

 purea, S. alba, S. lambertina, S. incana, 

 S. fissa, S. has fata, S. poly and ra, S.fra- 

 gilis, S. amygdalina, 8. pentandra, S. prce- 

 cox, &c.), in poplar \Populus tremnla, 

 P. alba, P. balsamifera, and P. graca), 

 and in flower buds of the meadowsweet 

 (Spirtea ulmaria}. 



Salicin is found also in the buds of 

 Populns pyramidalis, P. nigra, and P. 

 monilifera. (For liberation of saligenin 

 from salicin see Piria, Ann. 56, 37 : for 

 distribution of salicin in vegetable 

 kingdom, Leroux, Ann. Ch. [2] 43, 

 440; Tischhauser, Ann. 7, 280; Bra- 

 connot, Ann. Chim. [2] 44, 296 ; 

 Pelouze and Gay-Lussac, Ibid. 22O; 

 48, ill ; Piria, Ibid. 69, 281 ; [3] 14, 

 257; Gerhardt, Ibid. [3] 7, 215; 

 Bouchardat, Comp. Rend. 18, 299 ; 19, 

 602 ; H79; 20, 610 ; 1 635 ; in Spiraa 

 flowers, Buchner, Ann. 88, 224 : see 



