Acetone diethyl ketal

Enamines containing one -hydrogen atom react with the lactone dimer of dimethylketene to form aminocyclohexanediones 116). Polycondensation of acetone diethyl ketal takes place by treating it with morpholine and a catalytic amount of p-toluenesulfonic acid while distilling off the ethanol formed 117-119). The resulting spiran, bicyclo, and cyclooctadienone products differ from the known polycondensation products of acetone, and hence their formation probably involves enamine intermediates 119). 

Acetone anil cannot be obtained by direct reaction of the components mesityl oxide is formed and this reacts with the aniline to give l,2-dihydro-2,2,4-trimethylquinoline.887 However, the anil is formed smoothly when acetone diethyl ketal is condensed with aniline.888 The latter reaction is, however, not generally applicable because many acetals and ketals are unusually resistant to attack by ammonia or amines.505... 

Mercaptals from acetals. Acetone diethyl ketal and ethyl mercaptan heated 12 hrs. at 120-130° in a sealed tube acetone diethyl mercaptal. Y 80.7%. Also triethyl trithioorthoformate s. M. F. Shostakovskh et al., Izvest. 1960, 1901 G. A. 55, 16407c. 

A mixture of benzhydroxamic acid, acetone diethyl ketal, p-toluenesulfonic acid, and ethyl acetate refluxed 2.5 hrs. -> 2,2-dimethyl-5-phenyl-l,3,4-dioxa-zole. Y 75%. F. e. s. H. Nohira et al., Bull. Ghem. Soc. Japan 40, 664 (1967). 

When cyclobutadiene is liberated as a transient species by oxidative decomposition of cyclobutadieneiron tricarbonyl (lead tetraacetate in pyridine) in the presence of cyclopentadicnone diethyl ketal the adduct I is obtained. Irradiation of 1 in acetone gives 9,9-diethoxyhomocubane, which on hydrolysis gives homocubanone. II. The corresponding alcohol, homocubanol. is of interest because the derived cation is a fluctional molecule.2... 

Fig. 96. Application of TLC in the control of the synthesis of radioactively labelled chimyl alcohol (a-hexadecyl glycerol ether) from palmitic acid-1[425]. (see reaction scheme above) Layer silica gel G solvent petrol ether (BP 60—70° C)-diethyl ether-acetic acid (80 - - 20 + 1) time of run 1 h autoradiograph. 1 palmitic acid 2 methyl palmitate 3 crude pahnityl alcohol 4 recrystallised palmityl alcohol 5 filtrate from (3) 6 crude palmityl mesylate 7 recrystallised palmityl mesylate 8 filtrate from 6) 9 crude acetone ketal of chimyl alcohol 10 crude chimyl alcohol 11 recrystallised chimyl alcohol 12 filtrate from 10)...

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