15 A-E.] 



NORMAL PROPYL ALCOHOL 



59 



gives acrylic acid (Moureu, Ann. Chim. 

 [7] 2, 158 ; see also Schneider and 

 Erlenmeyer, Ber. 3, 339; Wislicenus, 

 Ann. 166, 2). 



Or ethylene combines with hypo- 

 chlorous acid to form glycolchlorbydrin 

 (Carius, Ann. 126, 197 ; Butleroff, Ann. 

 144, 40 : practically glycol from ethyl- 

 ene may be treated with hydrogen 

 chloride). The chlorhydrin with potas- 

 sium cyanide [172] and by hydrolysis of 

 the nitrile gives hydracrylic acid (Wisli- 

 cenus, Ann. 128, 4 ; 167, 346 ; Erlen- 

 meyer, Ann. 191, 268). The salts of 

 the latter give acrylic acid on dry 

 distillation (Beilstein, Ann. 122, 372). 

 From acrylic acid via glyceric acid and 

 pyrotartaric acid as above. 



NOTE : By these processes all generators of 

 ethyltne become generators of n-propyl alcohol. 



Or from ethyl alcohol and trioxy- 

 methylene \_formic aldehyde : Ol] by the 

 interaction of magnesium ethobromide 

 and trioxymethylene in ethereal solution 

 (Grignard and Tissier, Comp. Rend. 

 134. 107). 



[B.] From isopropyl alcohol [16] 

 through isopropyl iodide, which gives 

 propane by reduction with zinc and acid 

 (Schorlemmer, Ann. 150, 209). Or from 

 isopropyl alcohol through propylene 

 and conversion of latter into pyrotartaric 

 nitrile (by means of potassium cyanide 

 [172]) and pyrotartaric acid (see under 

 aipentene [9 ; F]) and then as under A. 



[C.] From normal butyl alcohol [17] 

 through n-butyl iodide, n-butylene by 

 the action of alcoholic potash on the 

 latter (Saytzeff, Journ. pr. Ch. [2] 3, 

 88; Lieben and Rossi, Ann. 158, 164; 

 Grabowsky and Saytzeff, Ann. 179, 330), 

 and secondary butyl iodide 2-iodo- 

 butane by combining the n-butylene 

 with hydrogen iodide (Wurtz, Ann. 

 152, 23). 2-Iodobutane gives propane 

 among other products on heating with 

 aluminium chloride above 160 (Lothar 

 Meyer, Ber. 27, 2766 ; Kluge, Ann. 

 282, 227). 



[D.] From tertiary butyl alcohol [19] 

 through tertiary butyl iodide, which 

 also gives propane when heated with 

 aluminium chloride as above (Lothar 

 Meyer, loc. cit. ; Kluge, loc. cit.). 



[E.] From glycerol [48], which gives 

 propane on heating in a closed vessel 

 with strong aqueous hydriodic acid 

 (Berthelot, Bull. Soc. [2] 7, 60; 9, 13; 

 184). 



Or through allyl alcohol by distilling 

 glycerol with oxalic acid (see under 

 ethyl alcohol [14; G]). Allyl alcohol 

 gives n-propyl alcohol on reduction with 

 zinc and dilute sulphuric acid (Linne- 

 mann, Ber. 7, 852), on heating with 

 solid potash (Tollens, Ann. 159, 92 ; 

 Zeit. [2] 7, 242), or by reduction with 

 aluminium in alkaline solution (Spe- 

 ranski, Journ. Russ. Soc. 31, 423). 



Glycerol gives n-propyl alcohol among 

 the products of decomposition of the 

 sodium compound above 245 (Fernbach, 

 Bull. Soc. [2] 34, 146). 



Or from glycerol through allyl brom- 

 ide (Henry, Zeit. [2] 6, 575; Tollens, 

 Ann. 156, 152 ; Grosheintz, Bull. Soc. 

 [2] 30, 98 ; Jacobi and Merling, Ann. 

 278, 11), trimethylene bromide by com- 

 bination with hydrogen bromide (Gero- 

 mont, Ann. 158, 370 ; Reboul, Ann. 

 Chim. [5] 14, 472 ; Erlenmeyer, Ber. 

 12, 1354; Roth, Ber. 14, 1351 ; Bogo- 

 molitz, Bull. Soc. [2] 30, 23), tri- 

 methylene = cyclopropane by the action 

 of sodium or of zinc dust on trimethylene 

 bromide in alcohol (Freund, Monats. 3, 

 626; Journ. pr. Ch. [2] 26, 367; see 

 also Reboul, Ann. Chim. [5] 14, 488 ; 

 Gustavson, Journ. pr. Ch. [2] 36, 300 ; 

 5O, 38 [ ; 59, 302 ; Journ. Russ. Soc. 

 19, 495 ; Comp. Rend. 128, 437 ; 

 Wagner, Ber. 21, 1 236 ; Tornoe, Ibid. 

 1282; Wolkoff and Menschutkin, Ber. 

 31, 3072; Journ. Russ. Soc. 32, 118; 

 Tanatar, Ber. 32, 702 ; 1965). Tri- 

 methylene combines with strong sul- 

 phuric acid to form dipropyl sulphate 

 (Freund), which gives n-propyl alcohol 

 on decomposition by hot water (Gustav- 

 son; Berthelot, Ann. Chim. [7] 4, 102). 

 Or trimethylene combines with hydro- 

 gen iodide to form n-propyl iodide, from 

 which the alcohol can be obtained by 

 the usual methods (Freund). 



Or from glycerol through acrolein 

 [lOl] (see also undercymene [6 ; X VIII]) 

 and oxidation of latter to acrylic acid 

 (Clans, Ann. Suppl. 2, 123; also Red- 

 tenbacher, Ann. 47, 125). From acrylic 



