68 



ALCOHOLS 



[16 P-AA. 



[P.] From dextrose [157], acetyl 

 carbinol being among the products of 

 fusion with alkali (Emmerling and 

 Loges, Ber. 10, 837). According to 

 Bouchardat (Comp. Rend. 73, 1008; 

 Ann. Chim. [4] 27, 68) isopropyl alco- 

 hol is among the products of reduction 

 of dextrose by sodium amalgam. 



[Q.] From pulegone [128] through 

 pyrotartaric acid (15 ; L). 



[B.] From menthone [129] through 

 pyrotartaric acid (15 ; M). 



[S.] From acetic acid [Vol. II], pro- 

 pylene being among the products formed 

 by passing the vapour over heated zinc 

 dust (Jahn, Ber. 13, 2111). 



Or from acetic acid and potassium 

 cyanide [172] and ethyl alcohol [14] 

 through pyrotartaric or ethylmalonic 

 acid (15 ; O) and then as above under 

 A and J. 



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

 through the amide, nitrile, and n-pro- 

 pylamine (15 ; N") and then as above 

 under C. Or from propionic acid 

 through pyrotartaric acid (15 ; N). 



[U.] From butyric acid [Vol. II], 

 isopropyl butyrate being among the 

 products of electrolysis of the acid 

 potassium salt (15 ; P). Or from 

 butyric acid through n-propylamine 

 (15 ; P) and then as above under C. 



Or from butyric acid through pro- 

 pane (15 ; P) and then as above under 

 B. Or from butyric acid through 

 crotonic to pyrotartaric acid (15 ; P) 

 and then as above under A. Or from 

 butyric acid and ethyl alcohol [14] 

 (and potassium-mercuric cyanide) through 

 ethylmalonic acid (15 ; P) and then as 

 above under J. 



Butyric acid gives propylene when 

 passed over hot zinc dust (Jahn, Ber. 

 13, 2115). Propylene is also among 

 the products of electrolysis of a solution 

 of potassium butyrate (Bunge, Journ. 

 Russ. Soc. 21, 552; Hamonet, Comp. 

 Rend. 123, 252 ; Petersen, Ch. Centr. 

 1897, 2, 519). From propylene as 

 above under B. 



[V.] From isobutyric acid [Vol. II] 

 through isopropylamine by the action 

 of bromine in the presence of alkali 

 on isobutyramide (Hofmann, Ber. 15, 

 768). From the amine as above under 



A and C. Isopropyl isobutyrate and 

 propylene are among the products of 

 electrolysis of a solution of potassium 

 isobutyrate (15 ; P ; also under IT 

 above). Isopropyl alcohol is among 

 the products of electrolysis of sodium 

 isobutyrate in presence of sodium per- 

 chlorate (Hofer and Moest, Ann. 323, 

 284). 



Or from isobutyric acid through 

 diisopropyl ketone by distillation of the 

 calcium salt (Popoff, Ber. 6, 1255; 

 Munch, Ann. ISO, 327). The oxime 

 of the ketone is transformed by acetyl 

 chloride into isopropyl -isobutyramide, 

 which gives isopropylamine (with iso- 

 butyric acid) on hydrolysis (Meyer and 

 Warrington, Ber. 20, 500). 



Also from isobutyric acid through 

 propane (15 ; Q). 



[W.] From isovaleric acid [Vol. II], 

 propylene being among the products 

 of pyrogenic decomposition (Hofmann, 

 Journ. Ch. Soc. 3, 121). Propylene 

 is among the products of the dry distil- 

 lation of calcium isovalerate (Dilthey, 

 Ber. 34, 2115). Or from isovaleric 

 acid through hydroxy pyrotartaric, citra- 

 conic, and pyrotartaric acids (benzyl 

 alcohol [54 ; M]). 



[X.] From lactic acid [Vol. II], which 

 gives propylene among the products 

 of distillation of the calcium salt (Gos- 

 sin, Bull. Soc. [2] 43, 49). Or from 

 lactic acid through acrylic or citraconic 

 acid to pyrotartaric acid (15 ; B). 



[Y.] From hydracrylic acid [Vol. II] 

 through acrylic acid to pyrotartaric 

 acid (15 ; S). 



iZ.] From fi-hydroxybutyric acid [Vol. 

 through crotonic acid to nitro- 

 propane and n-propylamine (15 ; IT) 

 and then as above under C. 



[AA.] From oxalic and acetic acids 

 [Vol. II], propylene being among the 

 products of dry distillation of a mixture 

 of calcium oxalate and potassium acetate 

 (Dusart, Ann. 97, 127). Or from oxalic 

 and acetic acids and ethyl alcohol [14] 

 through pyrotartaric or through ethyl- 

 malonic acid (15 ; Z). Or from oxalic 

 and propionic acids and alcohol [14] 

 through /3-methylmalic to citraconic 

 and pyrotartaric acid (benzyl alcohol 

 [54 j M]). 



