50 G-V.] 



ERYTHRITOL 



103 



alcohol gives 8-phenoxybutylamine, and 

 the latter on heating- with strong hydro- 

 chloric acid at 180-185 8-chlorbutyl- 

 amine (Ibid. 3232). On distilling the 

 amine with potash solution pyrrolidine 

 is formed (Ibid. 3234 ; Schlinck, Ber. 32, 

 1025) and the latter might be methy- 

 lated and treated as above under C. 



Or from glycerol through allyl alcohol 

 (see under ethyl alcohol [14 ; G]), which 

 probably gives di vinyl among the pro- 

 ducts of pyrogenic contact decomposition 

 (Ipatieff, Ber. 35, 1054). 



[H.] From Icevulose [155] through 

 Isevulic acid by boiling with dilute 

 sulphuric acid (Grote and Tollens, Ann. 

 175, 181) and subsequent treatment as 

 under D. 



[I.] Mannose [156] gives lavulic 

 acid when its phenylhydrazone is heated 

 with hydrochloric acid (Fischer and 

 Hirschberger, Ber. 22, 370). 



[J.] From dextrose [154] through 

 saccharic acid by oxidation with nitric 

 acid or bromine (Trommsdorff, Ann. 

 8, 36 ; Guerin-Varry, Ann. Chim. [2] 

 49,280; 52,318; 65,332; Herzfeld, 

 Ann. 220, 352 ; Tollens, Ann. 249, 

 2 1 8). Ammonium saccharate gives 

 pyrrole on distillation (Bell and Lapper, 

 Ber. 10, 1962), and this can be con- 

 verted into dimethylpyrrolidine, &c., as 

 under C. 



Or from dextrose through gluconic 

 acid [Vol. II], d-arabinose, and d- 

 erythrose (see under latter [152 ; D]). 

 The latter gives i-erythritol on reduc- 

 tion with sodium amalgam (Ruff, Ber. 

 32, 3677). 



[K.] From diethylamine [Vol. II]. 

 Pyrrole is formed when the vapour is 

 passed through a hot tube (Bell, Ber. 

 10, 1868), and can be treated as under C. 



[L.] From glutamic acid [Vol. II] 

 by converting the acid into pyroglu- 

 tamic acid by heating to 190, the 

 latter on further heating giving pyrrole 

 (Haitinger, Monats. 3, 228). 



[M.] From piperidine [Vol. II] 

 through dimethylpiperidine by heating 

 the hydrochloride with methyl alcohol 

 at 250 and decomposition of the 

 ammonium chloride derivative by 

 silver oxide, &c. (Ladenburg, Ber. 

 16, 2057; Ladenburg, Mugdan, and 



Brzostovicz, Ann. 279, 344). Di- 

 methylpiperidine hydrochloride when 

 treated with hydrogen chloride at 220 

 is converted into dimethylpyrrolidine 

 (Ladenburg, Mugdan, and Brzostovicz, 

 loc. cit.\ also Merling, Ann. 264, 310), 

 which can be converted into erythrene 

 as under C, &c. 



[N.] Dimethyllieptenol [35] gives Ia3- 

 vulic acid among the products of its 

 oxidation by chromic acid mixture (Bar- 

 bier, Comp. Rend. 126, 1424). 



[O.] From crotonic aldehyde [102] and 

 hydrogen cyanide [172]. The cyanhydrin 

 of crotonic aldehyde hydrolyses to a- 

 hydroxypentenoic acid [CH 3 . CH : CH . 

 CH(OH) . COOH], and this on heating 

 with dilute hydrochloric acid undergoes 

 (isomeric) transformation into Iffivulic 

 acid (Fittig, Ber. 29, 2582 : see also 

 Lobry de Bruyn, Bull. Soc. [2] 42, 

 159; Fittig, Ann. 299, i). 



[P.] From furfural [126] through 

 pyromucic acid by oxidation (Schwanert, 

 Ann. 114, 63 ; 116, 257 ; Volhard, Ann. 

 261, 379). The acid on heating with 

 lime and ammonio-zinc chloride gives 

 pyrrole (Canzoneri and Oliveri, Gazz. 

 16, 487). From pyrrole to erythrene 

 as above under C. 



[Q.] Methylheptenone [ill] on oxida- 

 tion with potassium permanganate gives 

 a ketone glycol which, on further oxida- 

 tion with chromic and sulphuric acid, 

 yields (with acetone) Ia3vulic acid (Tie- 

 mann and Semmler, Ber. 28, 2128). 



[B.] From d-erythrose [152] by re- 

 duction as above under J. 



[S.] Azela'ic acid [Vol. II] gives ery- 

 threne among the products of its dis- 

 tillation with soda-lime (Miller and 

 Tschitschkin, Journ. Russ. Soc. 31, 414 ; 

 Ann. 307, 375). 



[T.] From gluconic acid [Vol. II] 

 through d-arabinose and d-erythrose as 

 above under J. 



[U.] From pyrrole [Vol. II] and 

 met/tyi alcohol [13] as above under C. 



[V.] Isopropyi alcohol [16] gives 

 divinyl (erythrene) among the products 

 of pyrogenic contact decomposition (Ipa- 

 tieff:, Ber. 35, 1056). 



NOTE : The biochemical product, d-erythru- 

 lose [152], obtained from i-erythritol by the 

 action of the sorbose Bacterium, gives with the 



