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ACETOPHENONE

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Originally appearing in Volume V01, Page 137 of the 1911 Encyclopedia Britannica.
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ACETOPHENONE , or PHENYL-METHYL KETONE, C8H80 or C6H5CO•CH3, in See also:

chemistry, the simplest representative of the class of mixed aliphatic-aromatic See also:ketones. It can be prepared by distilling a mixture of dry See also:calcium benzoate and acetate, Ca(02CC6H5)2+(CH3CO2)2Ca=2CaCO3+2C6H5CO•CH3, or by condensing See also:benzene with acetyl chloride in the presence of anhydrous See also:aluminium, chloride (C. See also:Friedel and J. M. Crafts), See also:C6H6+ CH,0001= HC1+ C6HSO00H3. It crystallizes in colourless plates melting at 20 C. and boiling at 202°C.; it is insoluble in See also:water, but readily dissolves in the See also:ordinary organic solvents. It is reduced by nascent See also:hydrogen to the secondary See also:alcohol C6H5•CH.OH.See also:CH3 phenyl-methyl-carbinol, and on oxidation forms benzoic See also:acid. On the addition of phenylhydrazine it gives a phenylhydrazone, and with See also:hydroxylamine furnishes an oxime CH3>C=N•OH melting at 590C. This oxime under-goes a See also:peculiar rearrangement when it is dissolved in See also:ether and See also:phosphorus pentachloride is added to the ethereal See also:solution, the excess of ether distilled off and water added to the See also:residue being converted into the isomeric substance acetanilide, C6H5NH000H3, a behaviour shown by many ketoximes and known as the See also:Beckmann See also:change (see Berk/de, 1886, 19, p. 988). With See also:sodium ethylate in See also:ethyl acetate solution it forms the sodium derivative of benzoyl See also:acetone, from which benzoyl acetone, C6H5•CO•CH2•CO•CH3, can be obtained by acidification with acetic acid. When heated with the See also:halogens, acetophenone is substituted in the aliphatic portion of the See also:nucleus; thus See also:bromine gives phenacyl bromide, C6H5CO• CH2Br.

Numerous derivatives of acetophenone have been prepared, one of the most import-See also:

ant being orthoaminoacetophenone, NH2• C6H4• CO• CH3, which is obtained by boiling orthoaminophenylpropiolic acid with water. It is a thick yellowish oil boiling between 242° C. and 250° C. It condenses with acetone in the presence of See also:caustic soda to a See also:quinoline. Acetonyl-acetophenone, C6H6•CO•CH2•CH2•CO•CH8, is produced by condensing phenacyl bromide with sodium acetoacetate with subsequent elimination of See also:carbon dioxide, and on dehydration gives aa-phenyl-methyl-See also:furfurane. Oxazoles (q.v.) are produced on condensing phenacyl bromide with acid-amides (M. Lewy, Berichte, 1887, 20, p. 2578). K. L. Paal has also obtained See also:pyrrol derivatives by condensing acetophenone-acetoacetic-ester with substances of the type NH2R.

End of Article: ACETOPHENONE

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