A Manual of the Chemistry of the Carbon Compounds

384 TEE CHEMISTRY OF
is obtained by the action of hot nitric acid on the ketone as an orangered,
syrupy liquid.
Secondary StyrohjlAlcohol, or Phenyl-mtkyl Carbinol^^ icttOH
is produced by the action of sodium-amalgam on an alcoholic solution
of the ketone. It crystallizes in long prisms, melting at 120°.
Phenylglycolyl Chloride C8H5.CO.CHSC1 is formed by passing
chlorine into the boiling ketone; it crystallizes in plates, melting at
41°, boiling at 246°, and possessing a pungent smell,
Plienylglycolyl Acetate CpH5.CO.CHa.0C2H8O has been prepared
by heating the chloride with alcoholic and potassium acetate. It
crystallizes in large rhombic plates, melting at 44°, and boiling at
270°. Alcoholic potash converts it into phenylglycolyl alcohol, which
has not been obtained in a pure state.
Phmytglycollio Add, or Manddic Arid C6H6.CH(OH).CO8H:, is
produced by heating an alcoholic solution of oil of bitter almonds,
pruasic acid and hydrochloric acid for some time to 90°, It is readil ••
soluble in water, and crystallizes in prisms, On heating it with
hydriodic acid, it is reduced to phenylacetic acid, and oxidizing
agents convert it into benzoic acid. Mandelic acid is isomeric with^
cresotic acid and tolyleneglycollic acid;—
Ctesotio Acid, Tolyleneglycollic Acid. Jlandolic Acid.
| ^ C6H6.CH(0H)CO4H
ETHBNTI.-BBNZENE, OB 8TTB0LENB C9H6.CgHg,
This hydrocarbon, which has also been called phenyl-ethene, occurs
iu the liquid styrax (from Styram oficinalia), and is isolated by distilling
this balsam with a solution of sodium carbonate to retain
cinnamic acid. It is also obtained by distilling cinnamio acid
C.Hs.C,Hj.CO«H with baryta, and by heating atyrolyl bromide with
alkalis or distilling secondary styrolyl alcohol with zinc chloride. It
appears to exist in coaltar, and is produced together with benzene
and other bodies when acetylene is heated to a dull-red heat.
Styrolene is a mobile, very refractive, and fragrant liquid, boiling
at 146°. When it is heated to 200°, it is converted into a polymeride,
called metastyrolene; this transformation also takes place slowly at
the ordinary temperature. By distillation it is reconverted into
styrolene,
Distyrolene C19H18is formed by heating styrolene with hydrochloric
acid to 170°; it is an oily liquid, which on distillation does not yield
styrolene.
The hydrocarbon existing in styrax is optically active, possessing a
right-handed rotatory power; but that obtained from cinnamic acid is