ACETOPHENONE

This article appears in Volume V01, Page 137 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: A10-ADA

ACETOPHENONE , or PHENYL-METHYL KETONE, C8H80 or C6H5COCH3, in chemistry, the simplest representative of the class of mixed aliphatic-aromatic ketones. It can be prepared by distilling a mixture of dry

calcium

CALCIUM [symbol Ca, atomic weight 40.0 (o= x6)]

benzoate and acetate, Ca(02CC6H5)2+(CH3CO2)2Ca=2CaCO3+2C6H5COCH3, or by condensing benzene with acetyl chloride in the presence of anhydrous

aluminium

ALUMINIUM (symbol Al; atomic weight 27.0)

, chloride (C.

Friedel

FRIEDEL, CHARLES (1832-1899)

and J. M. Crafts),

C6H6

C6H6

+ CH,0001= HC1+ C6HSO00H3. It crystallizes in colourless plates melting at 20 C. and boiling at 202C.; it is insoluble in water, but readily dissolves in the

ordinary

ORDINARY (med. Lat. ordinarius, Fr. ordinaire)

organic solvents. It is reduced by nascent hydrogen to the secondary alcohol C6H5CH.OH.CH3 phenyl-methyl-carbinol, and on oxidation forms benzoic acid. On the addition of phenylhydrazine it gives a phenylhydrazone, and with

hydroxylamine

HYDROXYLAMINE, NH2OH

furnishes an
oxime CH3>C=NOH melting at 590C. This oxime under-goes a peculiar rearrangement when it is dissolved in ether and phosphorus pentachloride is added to the ethereal solution, the excess of ether distilled off and water added to the residue being converted into the isomeric substance acetanilide, C6H5NH000H3, a behaviour shown by many ketoximes and known as the Beckmann

change

CHANGE (derived through the Fr. from the Late Lat. cambium, cambiare, to barter; the ultimate derivation is probably from the root which appears in the Gr. 冠 urmu', to bend)

(see Berk/de, 1886, 19, p. 988). With sodium ethylate in ethyl acetate solution it forms the sodium derivative of benzoyl

acetone

ACETONE, or DIMETHYL KETONE

, from which benzoyl

acetone

ACETONE, or DIMETHYL KETONE

, C6H5COCH2COCH3, can be obtained by acidification with acetic acid. When heated with the halogens, acetophenone is substituted in the aliphatic portion of the nucleus; thus bromine gives phenacyl bromide, C6H5CO CH2Br. Numerous derivatives of acetophenone have been prepared, one of the most import-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

caustic

CAUSTIC (Gr. rcavvraubs, burning)

soda to a

quinoline

QUINOLINE (Benzopyridine), C9H7N

. Acetonyl-acetophenone, C6H6COCH2CH2COCH8, is produced by condensing phenacyl bromide with sodium acetoacetate with subsequent elimination of carbon dioxide, and on dehydration gives aa-phenyl-methyl-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 pyrrol derivatives by condensing acetophenone-acetoacetic-ester with substances of the type NH2R.

End of Article: ACETOPHENONE

If you wish, you can link directly to this article.

<a href="http://jcsm.org/StudyCenter/Encyclopedia/A10_ADA/ACETOPHENONE.html">
ACETOPHENONE
</a>

(Previous)
ACETONE, or DIMETHYL KETONE

(Next)
ACETYLENE

JCSM was founded in 1997 and exists to help the community and bring people into a life-changing and productive relationship with Jesus Christ. JCSM offers over 200,000 free web pages, including its weekly inspirational emails that were sent continuously for over a decade.

Jesus Christ Saves Ministries
P.O. Box 9297
San Diego, CA 92169
1-888-887-0417 or Email