106 R-AA,] 



ACETONE 



199 



Or malonic ester, by the action of 

 sodium at 70-90, gives acetonetricar- 

 boxylic ester, and this yields acetone on 

 heating- with strong acids (Willstatter, 

 Ber. 32, 1274). 



[S.] From methyl and ethyl alcoli oh [13 ; 

 14] and hydrogen cyanide [172] through 

 propionitrile (Pelouze, Ann. 10, 249 ; 

 Williamson, Phil. Mag. [4] 0, 205 ; 

 Buckton and Hofmann, Journ. Ch. Soc. 

 9, 250 ; Rossi, Ann. 159, 79). The 

 latter, on treatment with sodium in 

 ethereal solution, gives a product which 

 by interaction with methyl iodide fol- 

 lowed by aqueous hydrogen chloride 

 yields ' trimethylpyrolone ' (C 7 H U NO). 

 The latter, on heating with strong 

 aqueous hydrogen chloride at 140-150, 

 gives ethylisopropyl ketone, from which 

 acetone is obtained by oxidation as under 

 K (E. v. Meyer, Journ. pr. Ch. [2] 38, 

 336 ; Hanriot and Bouveault, Com p. 

 Rend. 1O8, 1171 ; Bull. Soc. [3] 1, 549). 



Or from ethyl and methyl alcohols 

 through chloral and dimethylisopropyl 

 carbinol (see under tertiary butyl alcohol 

 [19 ; G]), and then as above under K. 



Or from methyl alcohol and hydrogen 

 cyanide through methyl cyanide (ace- 

 tonitrile). The latter interacts with 

 magnesium methobromide to form an 

 intermediate compound, which is de- 

 composed by acids with the formation 

 of acetone (general method of Blaise : 

 Comp. Rend. 132, 38). 



Or from ethyl alcohol through iodo- 

 form, acrylic acid, a-chlorlactic acid, and 

 glyceric acid (see under benzyl alcohol 

 [54; I]). From the latter through 

 pyrotartaric acid and allylene as under 

 benzyl alcohol [54; F and E], and above 

 under B; or through pyroracemic acid as 

 under benzyl alcohol [54; E], and above 

 under F and P. Allylene is formed 

 when the vapour of ethyl alcohol is 

 passed over heated magnesium and the 

 product decomposed by water (Keiser 

 and Breed, Ch. News, 71, 118; Keiser, 

 Am. Ch. Journ. 18, 328). 



Or from ethyl alcohol through pro- 

 pionitrile as above, and from the latter 

 through aa-diehlorpropionic acid and 

 pyroracemic acid as under benzyl alcohol 

 [54 ; l], and then as above under P. 



Or from ethyl alcohol and hydrogen 



cyanide through ethylene, vinyl chloride, 

 chloracetaldehyde,/3-chlorlactic acid, and 

 glyceric acid (see under benzyl alcohol 

 [54-; A]). From the latter, as above, 

 through pyrotartaric acid and allylene, 

 or through pyroracemic acid. 



NOTE : Other methods of passing from ethyl 

 alcohol through chloracetaldehyde to glyceric 

 acid are given under benzyl alcohol [54 ; I]. 



Generators of ethylene thus become (with 

 hydrogen cyanide) generators of acetone 

 through glyceric acid. 



[T.] From $-Jiydroxybutyric ac.'d [Vol. 

 II] through crotonic acid and allylene 

 (benzyl alcohol [54; L]), and then as 

 above under B. 



[U.] From erythritol [50] and formic 

 acid [Vol. II] through crotonic aldehyde 

 [102], crotonic acid and allylene (see 

 under n-butyl alcohol [17; I], and benzyl 

 alcohol [54; G]), and then as above 

 under B. 



[V.] Mvthylheplenone [ill] gives ace- 

 tone among the products of its oxida- 

 tion with chromic and sulphuric acids 

 (Tiemann and Semmler, Ber. 28, 2128). 



[W.] Dimethylheptenol [35] gives ace- 

 tone among the products of its oxidation 

 by chromic acid mixture ( Barbier, Comp. 

 Rend. 126, 1424). 



[X.] Ethane [14; D] and carbon 

 monoxide give an acetone (C 3 H 6 O) when 

 submitted to the action of the silent 

 electric discharge in a cooled apparatus 

 (De Hemptinne, Bull. Acad. Roy. Belg. 

 [3] 34, 275). The product has not 

 been identified specifically as 2-pro- 

 panone. 



[Y.] Citronellal [1O5] and citronellol 

 [38] give acetone (with /3-methyladipic 

 acid) on oxidation with potassium per- 

 manganate, followed by potassium di- 

 chromate and sulphuric acid (Tiemann 

 and Schmidt, Ber. 29, 908; Barbier and 

 Bouveault, Comp. Rend. 122, 673 : see 

 also Harries and Schauwecker, Ber. 34, 

 2981). 



[Z.] Pulegone [128] gives acetone 

 among the products of its decomposition 

 by heating with formic acid (Wallach, 

 Ann. 289, 338), or by oxidation with 

 potassium permanganate. 



[AA.] Dextrose [154] gives acetone 

 among the products of dry distillation 

 (Tollens, ' Handbuch d. Kohlenhydrate/ 



