15 L-P.] 



NORMAL PROPYL ALCOHOL 



61 



kownikoff, Ber. 33, 1909). Subsequent 

 steps as above under A. 



[M.] Menthone [129] gives pyrotar- 

 taric acid as above (Ibid.). 



[N.] From propionic acid [Vol. II] 

 through propionic anhydride, which 

 gives n-propyl alcohol on reduction 

 with sodium amalgam (Linnemann, 

 Ann. 148, 251; 160, 231 ; 161, 18 ; 

 see also Saytzeff, Zeit. [2^] Q, 105). Or 

 ammonium propionate on dry distilla- 

 tion gives propionamide, which on heat- 

 ing with phosphorus pentoxide gives 

 propionitrile = ethyl cyanide (Dumas, 

 Malaguti, and Leblanc, Ann. 64, 334; 

 see also Aschan, Ber. 31, 2344). The 

 latter can be reduced to propylamine 

 and treated as above under A. 



Or from propionic acid through pro- 

 pionyl chloride, /3-chlorpropionyl chlo- 

 ride by chlorination and /3-chlorpropionic 

 acid by hydrolysis (Michael and Garner, 

 Ber. 34. 4046). From the /3-chloro- 

 acid through acrylic acid to pyrotar- 

 taric acid as above under A. 



Or from propionic acid through the 

 aa-dibromo-acid and the a/3-dibromo- 

 acid by transformation of the latter (see 

 under benzyl alcohol [54 ; O]). From 

 the a/3-dibromo-acid through glyceric 

 to pyrotartaric acid (Ibid.) and then as 

 above under A. 



Or from propionic and formic acid 

 [Vol. II] through propionic aldehyde 

 by distilling a mixture of the calcium 

 salts (Williamson, Journ. Ch. Soc. 4, 

 138 ; Lieben and Rossi, Ann. 158, 

 137; 159, 58; 79; 165, 109; 167, 

 293 ; Lieben and Janecek, Ann. 187, 

 126). The aldehyde gives the alcohol 

 on reduction (Rossi, Comp. Rend. 70, 

 129; Ann. 159, 80). Propaldoxime 

 also gives nitropropane among the pro- 

 ducts of oxidation by permonosulphuric 

 acid (Carols reagent; Bamberger and 

 Scheutz, Ber. 34, 2032). From nitro- 

 propane through propylamine as above 

 under I and A. 



NOTE : Generators of propionic aldehyde are 

 given under hexanal (a-methylpentanal [96 ; 

 C, Ac.]). 



[O.] From acetic acid [Vol. II] and 

 hydrogen cyanide [172] through acetyl 

 cyanide, pyroracemic (pyruvic), and 



pyrotartaric acid (see under benzyl 

 alcohol [54 ; l]). Then as above under 

 A. 



Or from acetic acid and potassium 

 cyanide through cyanacetic acid by the 

 interaction of chloracetic acid and the 

 cyanide (Miiller, Ann. 131, 348; 350; 

 Meves, Ann. 143, 201 ; Fiquet, Ann. 

 Chim. [6] 29, 439). The sodium deri- 

 vative of cyanacetic ester interacts with 

 ethyl iodide to form a-cyanobutyric 

 ester (Henry, Bull. Soc. [2] 48, 656 ; 

 Comp. Rend. 104, 1618), which gives 

 ethylmalonic acid as below under P and 

 n-propyl alcohol as under T. 



[P.] Normal butyric acid [Vol. II] 

 gives n-propyl butyrate when the silver 

 salt is acted upon by iodine (Simonini, 

 Monats. 14, 81), when the acid is oxi- 

 dised by manganese dioxide and dilute 

 sulphuric acid (Veiel, Ann. 148, 164), 

 or by the electrolysis of the solution of 

 the acid potassium salt (with some iso- 

 propyl butyrate in latter process ; Ha- 

 monet, Comp. Rend. 123, 252 ; Peter- 

 sen, Ch. Centr. 1897, 2, 519; 1900, 2, 

 172). The ester gives the alcohol by 

 hydrolysis. The alcohol is among the 

 products of electrolysis of sodium butyr- 

 ate in presence of sodium perchlorate 

 (Hofer and Moest, Ann. 323, 284). 



Or from butyric acid through butyr- 

 amide by distilling the ammonium 

 salt (Hofmann, Ber. 15, 982). The 

 amide gives n-propylamine by the action 

 of bromine in presence of caustic potash 

 (Ibid. 769). From the amine to the 

 alcohol as above under A. 



Butyric acid also gives propane by 

 photochemical decomposition in the 

 presence of uranium nitrate (Wisbar, 

 Ann. 262, 235). 



Or butyric acid by bromination gives 

 a-brombutyric acid (Gorup-Besanez and 

 Klincksieck, Ann. 118, 248 ; Naumann, 

 Ann. 119, 115; Borodin, Ibid. 123; 

 Friedel and Machuca, Ann. 12O, 279; 

 Suppl. 2, 70 ; Ley, Journ. Russ. Soc. 

 9, 129 ; Wislicenus and Urech, Ann. 

 165, 93 ; Tupoleff, Ann. 171, 249 ; 

 Genvresse, Bull. Soc. [3] 7, 366 ; 

 Michael and Graves, Ber. 34, 4041). 

 From a-brombutyric acid through nitro- 

 propane and propylamine, &c., as above 

 under I. 



