56 



ALCOHOLS 



[14 K-T. 



[K.] From octyl alcohol [28] through 

 iodoform (l ; Gr) and then as above. 



[L.] From butyric aldehyde [94] 

 through iodoform (l ; K) and then as 

 above. 



[M.] From acetone [106] through 

 chloroform or iodoform (l ; J). Iodo- 

 form gives acetylene or ethylene as 

 above. Chloroform gives acetylene by 

 passing the vapour over heated copper 

 (see under cymene [6 ; III]). Or 

 chloroform can be converted into methyl- 

 ene iodide by heating with aqueous 

 hydriodic acid at 1 30 (Bljuducho, Zeit. 

 [2] 1, 91). From methylene iodide to 

 ethylene as above under I. 



Or from acetone through bromof orm 

 (Lowig, Ann. 3, 395 ; Dumas, Ann. 

 Chim. [2] 56, I2O; Giinther, Arch. 

 Pharm. [3] 25, 373). The latter gives 

 ethylene by the action of alcoholic 

 potash (Hermann, Ann. 95, 211 ; Long, 

 Ann. 194, 23). 



Or from acetone through acrole'in 

 [lOl] and allyl alcohol (see under 

 glycerol [48 ; E]) and then as above 

 under Gr. 



[N.] From phenol [60], ethylene 

 being among the products of pyrogenic 

 decomposition (Miiller, Journ. pr. Ch. 

 58, i). Or from phenol through chlor- 

 aa-glyceric acid and chloroform (see 

 under methane [l; M]), and then through 

 acetylene, &c., as above under M. 



[O.] Yromcresol [61; 62; 63], ethyl- 

 ene being among the products of pyro- 

 genic decomposition (Muller, loc. cit.}. 



[P.] From dextrose [154], ethyl 

 alcohol being produced in small quan- 

 tity by the action of an alternating 

 electric current on an aqueous solution 

 (Berthelot, Ann. Chim. [5] 16, 450). 

 Ethyl alcohol is among the products 

 of reduction of dextrose by sodium 

 amalgam (Bouchardat, Comp. Rend. 

 73, 1008; Ann. Chim. [4] 27, 68). 



1 Sugar ' in alkaline solution is said 

 to yield alcohol under the influence 

 of light in the absence of all life 

 (Duclaux, Ann. Inst. Past. 10, 168). 



[Q.] From hydrogen cyanide [172] or 

 metallic cyanides, these by interaction 

 with red-hot magnesium giving mag- 

 nesium carbide. The latter is decom- 

 posed by water with the formation of 



acetylene (Eidmann, Journ. pr. Ch. [2] 

 59, ]). 



[B.] From formic acid [Vol. II] and 

 methyl alcohol [13] through methyl for- 

 mate, perchlormethyl formate, and car- 

 bon tetrachloride (see under methane 

 [1; O]). The latter on heating with 

 strong aqueous hydriodic acid at 130 

 gives iodoform (Walfisz, Bull. Soc. [3] 

 7, 256), from which acetylene, &c., can 

 be obtained as above under I. Barium 

 formate gives ethylene among the pro- 

 ducts of dry distillation (Watts' Diet. 

 II, 484; comp. Merz and Weith, Ber. 

 15, 1511). 



[S.] From acetic acid [Vol. II] 

 through acetyl chloride or acetic anhy- 

 dride and reduction with sodium amal- 

 gam (Linnemann, Ann. 148, 249 ; 

 Saytzeff, Journ. pr. Ch. [2] 3, 76). 

 Or indirectly through ethane by electro- 

 lysis (Kolbe, Ann. 69, 279; Kuenen, 

 Proc. Physical Soc. 15, 237) and then 

 through ethyl chloride, &c., as above 

 under D. 



Ethylene is among the products 

 formed by dropping acetic acid on to 

 heated zinc chloride (LeBel and Greene, 

 Am. Ch. Journ. 2, 26), and among the 

 products of electrolysis of an acid solu- 

 tion of potassium acetate (Petersen, Ch. 

 Centr. 1897, 2, 518). 



A solution of the potassium salts of 

 acetic and gly collie acid [Vol. II], the 

 acetate being at the anode, give alcohol 

 on electrolysis (v. Miller and Hofer, 

 Ber. 28, 2437). 



Or from acetic acid through ethyl- 

 amine [Vol. II] and then as under FF 

 below. 



[T.] From propionic acid [Vol. II], 

 which gives ethane by photochemical 

 decomposition in presence of uranium 

 salts (Fay, Am. Ch. Journ. 18, 269). 

 Ethyl propionate is formed by the elec- 

 trolysis of an acid solution of potassium 

 propionate (Peterseu, Ch. Centr. 1897, 

 2, .5i8). _ 



Ethyl iodide is formed by the elec- 

 trolysis of sodium propionate with 

 potassium iodide for the negative elec- 

 trolyte (v. Miller and Hofer, Ber. 28, 

 2430). Ethylene is among the pro- 

 ducts of electrolysis of a neutral solution 

 of potassium propionate (Bunge, Journ. 



