200 ALDEHYDES AND KETONES : FATTY GROUP [lO6 AA-107 A. 



I, 46), and among the products of oxida- 

 tion by hydrogen peroxide (Cotton, Journ. 

 Pharm. 10, 195), or of dry distillation 

 with lime (Pereire and Guignard, Fr. 

 Pat. 316060 of 1901; Journ. Soc. Ch. 

 Ind. 21, 1096). 



[BB.j From aconitic acid [Vol. II] 

 through itaconic acid (Pebal, Ann. 98, 

 94), allylene (see under benzyl alcohol 

 [54; M]), and then as above under B. 



[CO.] From mannitol [5l] through 

 acrole'in [lOl] and acrylic acid (see under 

 benzyl alcohol [64; B and AA])> and 

 then as above under S. 



Acetone is among the products of 

 fusion of mannitol with alkali (Gotfc 

 lieb, Ann. 52, 122), and of oxidation by 

 hydrogen peroxide (Cotton, Journ. 

 Pharm. 10, 195). 



[DD.] Isobutyric aldehyde [94], on 

 treatment with caustic potash, forms a 

 trimeric polymeride (Pfeiffer, Ber. 5, 

 700 ; Urech, Ber. 12, 191 ; W. H. 

 Perkin, junr., Trans. Ch. Soc. 43, 91), 

 which, on bromination (in CS 2 ) and by 

 the action of heat on the polymeride, gives 

 a-bromisobutyric aldehyde = 2-methyl- 

 2-brompropanal. The oxime of the 

 latter, on heating with acetic anhydride, 

 yields a nitrile which is decomposed by 

 sodium carbonate solution with the for- 

 mation of acetone (Franke, Monats. 

 21, 205 ; 210). 



Or isobutyric and acetic aldehydes con- 

 dense to form an aldol (C e H 12 O 2 ), which, 

 on oxidation with potassium permangan- 

 ate, gives trimethylethylene lactic acid 

 (Lilienfeld and Tauss, Monats. 19, 81). 

 From the latter; through tertiary amyl 

 alcohol, &c., as above under K and E. 



Or isobutyric and formic aldehydes 

 condense to form a glycol, which gives 

 methylisopropyl ketone among the pro- 

 ducts of decomposition by heating with 

 water (Lieben, Monats. 23, 60). From 

 the ketone as under K above. 



Or isobutyric aldehyde condenses in 

 contact with alkali with the formation 

 of diisopropylglycol = 2:2: 4-trimethyl- 

 pentanediol, and this gives diisopropyl 

 ketone on oxidation with potassium per- 

 manganate (Fossek, Monats. 4, 664 ; 

 Brauchbar, Ibid. 17, 641 ; Franke, Ibid. 

 673). The ketone yields acetone on 

 further oxidation as under K above. 



[EE.] Phloroglucinol [86] gives ace- 

 tone among other products on heating 

 with 25 per cent, caustic potash solu- 

 tion at 1 60 (Combes, Bull. Soc. [3] 11, 

 716). 



[FF.] Ckelidomc acid [Vol. II] gives 

 acetone (and oxalic acid) on heating 

 with aqueous alkali (Lieben and Haitin- 

 ger, Ber. 16, 1259). 



[GG.] Mentkone [129] gives an oxime 

 and the latter a nitrile, which can be 

 converted into an aldehyde isomeric 

 with citronellal. The aldehyde, on oxida- 

 tion, yields first menthonic acid and 

 finally (/3-methyladipic acid and) ace- 

 tone (Wallach, Ann. 278, 302; 296, 



[HH.] Acetyl carbinol [43] gives ace- 

 tone when reduced in acid solution in 

 the cold (Kling-, Comp. Rend. 135, 

 970). 



107. Metliyl-ii-amyl Ketoiie ; 

 2-Heptanone. 



CH 3 .CO.[CH 2 ] 4 .CH 3 



NATURAL SOURCES. 



Occurs in small quantity in oil of 

 cloves (Schimmel's Ber. April, 1897, 

 and April, 1902; Ch. Centr. 1902,!, 

 1058 : see also Erdmann^ Journ. pr. Ch. 

 [2] 56, 155 ; Gerber, Mon. Sci. [4] 

 11, 880), and in Ceylon oil of cinnamon 

 (SchimmePs Ber. April, 1902 ; Wal- 

 baum and Hiithig, Journ. pr. Ch. [2] 

 66, 47). 



SYNTHETICAL PROCESSES. 



[A.] Normal heptane [2], on chlorina- 

 tion, gives (with n-heptyl chloride) 2- 

 chlorheptane (Pelouze and Cahours, Jah- 

 resber. 1863, 528; Schorlemmer, Ann. 

 136, 266 ; Morgan, Ann. 177, 307), 

 from which the secondary alcohol (2- 

 heptanbl) can be obtained by the usual 

 methods (Schorlemmer, Ann. 127, 315 ; 

 161, 278; Journ. Ch. Soc. 26, 319); 

 Morgan, loc. cit.). The alcohol gives 

 the ketone on oxidation (Schorlemmer, 

 Ann. 161, 279). 



Or n-heptane may be nitrated and the 

 2-nitroheptane reduced to methylamyl 



