15 U-AA.] 



NORMAL PROPYL ALCOHO 



[Vol. II], which gives crotonic acid on 

 distillation (benzyl alcohol [54 ; L]). 



[V.] From tar tar ic acid [Vol. II] 

 through pyrotartaric acid by heating 

 per se or with hydrochloric or acetic 

 acid (Fourcroy and Vauquelin, Ann. 

 Chim. [i] 35, 161 ; 64, 42; Rose, 

 Gehlen's Journ. 3, 598 ; Pelouze, Ann. 

 Chim. [2] 56, 297 ; Weniselos, Ann. 

 15, 148 ; Arppe, Ann. 66, 73 ; 90, 

 138; Geuther and Riemann, Zeit. [2] 

 5, 318; Bechamp, Ibid. [2] 6, 371 ; 

 Sacc, Ibid. 432 ; Bourgoin, Ann. Chim. 

 [5] 12, 419). From pyrotartaric acid 

 as above under A. 



[W.] From citric acid [Vol. II] 

 through citraconic,mesaconic,or itaconic 

 acid (see under benzyl alcohol [54 ; M]). 

 From these acids through pyrotartaric 

 acid (Ibid.}. 



NOTE : The following generators of citra- 

 conic acid given under benzyl alcohol [54 ; M] 

 thus become generators of n-propyl alcohol 

 through pyrotartaric acid : Lactic acid (see 

 above under R) ; acetoacetic ester and hydrogen 

 cyanide through hydroxypyrotartaric acid ; iso- 

 valeric acid through hydroxypyrotartaric acid ; 

 propionic and malonic acids through propanetri- 

 carboxylic = methylethenyltricarboxylic 

 ester ; acetic and propionic acids, ethyl alcohol and 

 potassium cyanide through a - methyl -#-cyano- 

 succinic ester ; oxalic and propionic acids and 

 ethyl alcohol through methyloxalacetic ester 

 and /3-methylmalic acid. 



The propanetricarboxylic acid above referred 

 to gives pyrotartaric acid directly (see under 

 benzyl alcohol [54 ; G]). 



Or from citric acid through acetone- 

 dicarboxylic acid (see under orcinol [75 ; 

 C]), which gives /3-oxyglutaric acid on 

 reduction (v. Pechmann and Jenisch, 

 Ber. 24, 3250). The latter on distilla- 

 tion in vacno gives vinylacetic acid 

 (Fichter and Krafft, Ber. 32, 2799; F. 

 and Sonneborn, Ber. 35, 938), which is 



a (anti-) oximinosuccinafeT^T^. 65), the 

 acid from which decomposes on heating 

 with water with the formation of cyan- 

 acetic acid (Cramer, Ber. 24, 1208). 

 The latter gives a-cyanobutyric acid, 

 ethylmalonic acid, Sec., as above under O. 



Or from succinic acid through the di- 

 bromo-acid by bromination (see under 

 methane [l ; T]). The dibromo-acid 

 gives ethoxyfumaric ester on treatment 

 with sodium ethoxide (Michael and 

 Bucher, Ber. 29, 1792). The ester 

 gives oxalacetic acid by the action of 

 hydrochloric acid (Ibid.} or alcoholic 

 potash (Nef, Ann. 276, 230). The ester 

 of oxalacetic acid gives pyrotartaric or 

 ethylmalonic acid as below under Z. 



[Z.] From oxalic and acetic acids 

 [Vol. II] and alcohol [14]. Diethyl 

 oxalate and ethyl acetate condense 

 by the action of sodium or sodium 

 ethoxide with the formation of diethyl 

 oxalacetate (Wislicenus, Ann. 246, 315 ; 

 Piutti, Gazz. 17, 520 ; Drude, Ber. 30, 

 952). The latter on heating with 10 

 per cent, sulphuric acid gives pyrora- 

 cemic and through this pyrotartaric 

 acid (Wislicenus, loc. cit.}. 



Or ethyl oxalacetate combines with 

 hydro xyltimine to form /3-(syn)-oximino- 

 succinic ester (Cramer, Ber. 24, 1206), 

 the acid from which decomposes on 

 heating with the formation of cyanacetic 

 acid (Ibid.}. Subsequent steps through 

 ethylmalonic acid as above. 



[AA.] From acetoacetic ester [Vol. 

 II] through acetyl cyanide and pyrora- 

 cemic acid (see under benzyl alcohol 

 [54; I]). From the latter through 

 pyrotartaric acid, &c., as above under 

 O, &c. 



Or from acetoacetic ester and a-6rom- 



readily transformed into crotonic acid propionic ester through /3-methylaceto- 



by the action of mineral acids. From 

 crotonic acid as above under I. 



[X.] From aeon/tic acid [Vol. II] 

 through itaconic acid (see under benzyl 

 alcohol [54; X]) and then through 

 pyrotartaric acid, &c., as above under W. 



[Y.] From succinic acid [Vol. II] and 

 alcohol [14] through succinylsuccinic 

 ester (see under quinol [71; N]). The 

 latter forms a dinitroso-derivative (Ebert, 

 Ann . 229, 55) , which on longcontact with 

 water yields ethyl isonitrososuccinate = 



succinic ester and pyrotartaric acid 

 (benzyl alcohol [54; l]). Or from 

 acetoacetic ester and chloracetic ester 

 through acetosuccinic ester, a-methyl- 

 acetosuccinic ester, and pyrotartaric acid 

 (54; I). 



Or from acetoacetic ester and methyl 

 iodide through methylacetoacetic ester 

 and mesaconic acid (54 ; I). From the 

 latter through pyrotartaric acid, &c., 

 as above under W. 



Or from acetoacetic ester and ethyl 



