A Manual of the Chemistry of the Carbon Compounds

364 THE CMSMI8TBY OF
BENZYL COMPOUNDS.
The radical Benzyl is contained In a series of compounds which in
many reactions exhibit the closest analogy with the compounds of the
monad alcohol-radicals. They differ, however, from the latter by containing
the aromatic nucleus, and forming, therefore, also products of
substitution, corresponding to the derivatives of benzene.
Benzyl Chloride C7H.,CH2C1 is easily obtained by passing the
required quantity of chlorine into boiling toluene, and purifying the
product by fractional distillation. It is a limpid, refractive liquid,
boiling at 176°.
Benzyl Bromide C9H6.CH»Br is produced by the action of bromine
on boiling toluene. It bom at 199°, and possesses an irritating
odour.
Benzyl Iodide C6H5.OH4I,—To prepare this compound, one part of
benzyl chloride is mixed with five parts of concentrated hydriodic
acid, and the mixture kept in the dark for three weeks, and frequently
ahaken. Pure benzyl iodide is a white crystalline solid, melting at
24°; it cannot be distilled, and decomposes at 240°. Its odour is very
irritating, and produces a copious flow of tears.
Benzyl Alcohol CaHa,CH2OH was first produced by treating its
aldehyde (oil of titter almonds) with alcoholic potash, which acts
violently upon it, half of the aldehyde being reduced to the alcohol,
and the other half oxidized to bonzoic acid:—
2C,;H5.COH + KOH = CflH8.CHi!.OH + C6H6.CO.OK
Benzyl alcohol is also formed by acting with nascent hydrogen on
the aldehyde or benzoic acid, and may be prepared by adding sodium
amalgam gradually to a boiling solution of benzoic acid. It has also
been produced by decomposing the acetate with caustic potash.
Benzyl alcohol is a liquid boiling at 207°, and possessing an
aromatic odour. Oxidizing agents convert it into benzaldehyde and
benzoic acid, and the hydracids of the chlorine-group transform it
into the corresponding haloid-ethers. On distillation with concentrated
potash-solution, it yields toluene and benzoic acid :—
2C6Hfc,CH8.OH = CaH6.GH8 + O6HB.CO.OH
0 IF CH }
Dihwnzyl Ether C 6 H B 'CH! f ^ nas ^ een P* 6 C ?**^ by heating the
6 H B
nlcohol with fused boron trioxide; it is an oily liquid, boiling
above 300°,
C H CH )
.Benzyl Acetate 6 QJ| Q$ }• 0 is readily produced by heating the
chloride or bromide with potassium or silver acetate, or by the action
of sulphuric acid on a mixture of acetic acid and benzyl alcohol, Ic
is an oily liquid, which possesses an agreeable odour, and boils
at 210°.