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CINNAMIC ACID, or PHENYLACRYLIC ACID,...

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Originally appearing in Volume V06, Page 376 of the 1911 Encyclopedia Britannica.
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CINNAMIC See also:

ACID, or PHENYLACRYLIC ACID, C9H802  or See also:C6H6•CH: CH•COOH, an See also:acid found in the See also:form of its benzyl ester in See also:Peru and Tolu balsams, in storax and in some gumbenzoins . It can be prepared by the reduction of phenyl propiolic acid with See also:zinc and acetic acid, by See also:heating benzal malonic acid, by the condensation of See also:ethyl acetate with See also:benzaldehyde in the presence of See also:sodium ethylate or by the so-called "See also:Perkin reaction "; the latter being the method commonly employed . In making the acid by this See also:process benzaldehyde, acetic an-hydride and anhydrous sodium acetate are heated for some See also:hours to about 18o C., the resulting product is made alkaline with sodium carbonate, and any excess of benzaldehyde removed by a current of See also:steam . The residual liquor is filtered and acidified with hydrochloric acid, when cinnamic acid is precipitated, See also:C6H5CHO+CH3000Na = C6HICH :CH • COONa+See also:H2O . It may be purified by recrystallization from hot See also:water . Consider-able controversy has taken See also:place as to the course pursued by this reaction, but the See also:matter has been definitely settled by the See also:work of R . See also:Fittig and his pupils (Annalen, 1883, 216, pp. too, 115; 1885, 227, pp . 55, 119), in which it was shown that the aldehyde forms an addition See also:compound with the sodium See also:salt of the fatty acid, and that the acetic anhydride plays the See also:part of a dehydrating See also:agent . Cinnamic acid crystallizes in needles or prisms, melting at 1330 C.; on reduction it gives phenyl propionic acid, See also:C6H5.See also:CH2•CH2•000H . Nitric acid oxidizes it to benzoic acid and acetic acid . Potash See also:fusion decomposes it into benzoic and acetic acids . Being an unsaturated acid it combines directly with hydrochloric acid, hydrobromic acid, See also:bromine, &c .

On nitration it gives a mixture of ortho and See also:

para nitrocinnamic acids, the former of which is of See also:historical importance, as by converting it into orthonitrophenyl propiolic acid A . See also:Baeyer was enabled to carry out the See also:complete See also:synthesis of See also:indigo (q.v.) . Reduction of orthonitrocinnamic acid gives orthoaminocinnamic acid, See also:C6H4(See also:NH2)CH:CH•000H, which is of theoretical importance, as it readily gives a See also:quinoline derivative . An isomer of cinnamic acid known as allo-cinnamic acid is also known . For the oxy-cinnamic acids see See also:COUMARIN .

End of Article: CINNAMIC ACID, or PHENYLACRYLIC ACID, C9H802
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