180 



ALDEHYDES AND KETONES : FATTY GROUP [92 S-CC. 



loff and Latschinoff, Ber. 7, 1387; 

 1777; Heintz, Ann. 174, 156; 175, 

 252 ; 181, 70). 



Diacetonamine salts also give mesityl 

 oxide (with diacetone alcohol) on treat- 

 ment with potassium nitrite (Sokoloff 

 and Latschinoff, loc. cit. ; Heintz, Ann. 

 178, 342). Diacetone alcohol also gives 

 mesityl oxide on treatment with strong 

 sulphuric acid (Heintz, Ann. 178, 351)- 



Or diacetonamine on oxidation with 

 chromic acid mixture gives a-aminoiso- 

 butyric acid (Heintz, Ann. 198, 46), 

 and this yields hydroxyisobutyric acid by 

 the action of nitrous acid (Tiemann and 

 Friedlander, Ber. 14, 1973), from which 

 aldehyde can be obtained as under K. 



[T.] Dextrose [154] gives acetic alde- 

 hyde among other products on oxidation 

 with sulphuric acid and manganese 

 dioxide (Liebig, Ann. 113, 16). 



'Invert sugar' (dextrose and Isevu- 

 lose) gives this aldehyde on electrolysis 

 of the aqueous solution in presence of 

 sulphuric acid (H. T. Brown, Journ. Ch. 

 Soc. 25, 578). 



[TL] Ethylamine [Vol. II] gives alde- 

 hyde among other products on oxidation 

 with chromic acid mixture (Wanklyn 

 and Chapman, Journ. Ch. Soc. 20, 

 328), and the oxime of the aldehyde 

 among the products of oxidation by 

 monopersulphuric acid (Bamberger, Ber. 

 35, 4293). 



[V.] Alanine [Vol. II] gives aldehyde 

 on boiling its aqueous solution with 

 lead peroxide, on heating per se, or on 

 heating with strong phosphoric acid 

 solution at 220 (Drechsel, Ber. 25, 



353)- 



[W.] Choline [Vol. II] on boiling in 



concentrated aqueous solution gives 

 glycol [45] and trimethylamine. From 

 the former aldehyde can be obtained as 

 under A. 



[X.] Furfural [126] on oxidation 

 gives pyromucic acid (Schwanert, Ann. 

 114, 63 ; 116, 257 ; Volhard, Ann. 261, 

 379), which on heating with bromine 

 at ]co yields 8-brompyromucic acid 

 (Hill and Sanger, Ann. 232, 46 ; Ber. 

 16, 1 130). The latter on heating with 

 bromine and water gives isodibrom- 

 succinic acid (H. and S. Ann. 232, 53), 

 which yields aldehyde as under P. 



[Y.] Citral [104] on boiling with 

 dilute alkali gives (with methylhepte- 

 none) acetaldehyde (Verley, Bull. Soc. 

 [3] 17, 175). 



[Z.] From citric acid [Vol. II] 

 through acetonedicarboxylic acid (see 

 under orcinol [75 ; C]). The latter by 

 the action of strong sulphuric acid 

 yields citracoumalic acid (Nieme and v. 

 Pechmann, Ann. 261, 199), and this 

 on heating at 200 gives the lactone 

 of mesitenecarbonic acid (Ibid. 202), 

 from which mesityl oxide can be 

 obtained as under L, hydroxyisobutyric 

 acid as under S, and aldehyde as 

 under K. 



Or from acetonedicarboxylic acid 

 through /3-oxyglutaric, vinylacetic, and 

 crotonic acid (see under n-propyl alco- 

 hol [15 ; W]), and then as above 

 under K. 



[AA.] From amyl alcoJiol from fusel 

 oil [22] through amylene = trimethyl- 

 ethylene (Balard, Ann. Chim. [3] 12, 

 320 ; Frankland, Journ. Ch. Soc. 3, 

 35 ; Wurtz, Bull. Soc. 5, 301), tri- 

 methylethylene bromide, and glycol (see 

 under acetone [106 ; E]). The latter 

 gives hydroxyisobutyric acid on oxida- 

 tion with nitric acid (Wurtz, Ann. 

 107, 197)- Subsequent treatment as 

 under K. 



Aldehyde is among the products of 

 oxidation of this amylene by potassium 

 permanganate, the glycol being formed 

 as an intermediate product (Wagner, 

 Ber. 21, 1235). 



Or from isoamyl alcohol through the 

 iodide, which gives secondary pentane 

 (4-methylbutane) on heating with zinc 

 and water (Frankland, Ann. 74, 53). 

 The pentane gives hydroxyisobutyric 

 acid among the products of the action 

 of nitric acid (Poni, Ch. Centr. 1902, 

 2, 1 6). 



[BB.] From oxalic acid [Vol. II] and 

 methyl alcohol [13] through hydroxyiso- 

 butyric acid (see under acetone [106 ; 

 O]), and then as above under K. 



[CC.] From methyl alcohol [13], 

 acetic aldehyde being among the pro- 

 ducts obtained by heating aluminium 

 methylate (Tistschenko, Journ. Russ. 

 Soc. 31, 784; Ch. Centr. 1900, 1, 



585). 



