A Manual of the Chemistry of the Carbon Compounds

392 THE CHEMISTRY OF
styrolene, and the residue boiled with a solution of sodium carbonate,
which removes the cinnamic acid. The residue is treated with cold
alcohol to dissolve the resins, and the remaining ethers are separated
by crystallization from a mixture of alcohol and ether or benzene.
The pure crystalline cinnyl cinnamate is boiled with concentrated
caustic potash, and thus cinnyl alcohol is obtained, crystallizing in
shining needles. It melts at 33°, boils at 250°, and possesses a
fragrant odour like hyacinths.
Cinnyl Chloride C0KfCJS.iC\ is obtained by heating the alcohol
with hydrochloric acid. It is a heavy, oily liquid, which possesses an
aromatic odour, and is decomposed by heat.
Cinnyl Iodide GMJG^JL is a similar body, and produced by treating
the nlcohol with iodine and phosphorus.
Cinnylamine C0H6.C,H4.NH2 is obtained by the action of alcoholic
ammonia on the chloride. It separates from ether in small crystals,
which on heating volatilize in vapours, possessing an alkaline odour.
CINIiAMYIi-COMPOUNDS.
Cinnamaldehyde CjH5.CjH5j.COH is the chief constituent of oil of
cinnuinon (from Pbrsea Cinnainomwni) and oil of cassia (from Persea
Cassia). It is produced artificially by oxidizing cinnyl alcohol with
platinum.black in the presence of air, and by distilling a mixture of
calcium cinnamate and formate. It has also been obtained by saturating
a mixture of benzaldehyde and acetaldehyde-with hydrochloric
acid. This reaction is quite analogous to the formation of erotonaldehyde
from ncetaldehyde (page 267):—
C9H6.CHO + CH8.C0H = C9H6.CH=CH—COH + H2O
' Pure cinnamaldehyde is obtained by agitating oil of cassia with
a concentrated solution of acid potassium sulphite; a crystalline
magma is formed, which is pressed, dried, washed with dilute alcohol,
and then decomposed with dilute sulphuric acid.
Ciunamaldehyde is a colourless, heavy, oily liquid, possessing a very
fragrant odour. It volatilizes without decomposition only in vacua or
with steam. It absorbs readily oxygen, and is converted into cinnaniic
add; dilute nitric and chromic acids oxidize it to benzaldehyde
and beuzoic acid.
Cianamie Acid, or Phmylacrylic Acid O6H6.CaHa,CO2H exists in
sfyrax, in balsam of Pern and Join, and in several kinds of gambenzoin.
It has been produced artificially by passing carbon dioxide
into a mixture of monobromcstyrolene and sodium, and by heating
oil of bitter almonds with acetyl chloride:—
(1) C,H5.C0H + CHa.COCl = C6H6.CH=CH.COC1
(2) C6H6.CH,^Cff.COCi + H2O = C6H6.OH=CH.CO.OH + HC1