This compound is readily oxidized to benzoic acid, C 6 H 5 000H, the aromatic residue being unattacked; nitric and sulphuric acids produce nitro-toluenes, C6H4 CH3 N02j and toluene sulphonic acids, C 6 H 4 CH 3 SO 3 H; chlorination may result in the formation of derivatives substituted either in the aromatic nucleus or in the side chain; the former substitution occurs most readily, chlor-toluenes, C 6 H 4 CH 3 Cl, being formed, while the latter, which needs an elevation in temperature or other auxiliary, yields benzyl chloride, C 6 H 5 CH 2 C1, and benzal chloride, C 6 11 5 CHC1 2.
Phenylnitromethane, C 6 H 5 CH 2 NO 2, isomeric with the nitrotoluenes, is prepared by the action of benzyl chloride on silver nitrite.
It is a colourless solid which melts at 92° C. For silicon derivatives of the amines see Michaelis, Ber., 1896, 29, p. 710; on asymmetric silicon and the resolution of dl-benzyl-ethyl-propyl-silicol see F.
Those substituted in the benzene nucleus are obtained by condensing two molecules of a substituted benzyl and benzal chlorides.
It is formed by the condensation of acetylene tetrabromide with benzene in the presence of aluminium chloride: Br CH Br CH C H +C6H6=4HBr+C6H4) I, )C6H4, Br CH Br CH and similarly from methylene dibromide and benzene, and also when benzyl chloride is heated with aluminium chloride to 200° C. By condensing ortho-brombenzyl bromide with sodium, C. L.
Soc., 1901, 79, p. 828) has resolved benzyl-allyl-phenyl-methylamine iodide by boiling with silver d-camphorsulphonate in a nearly anhydrous mixture of acetone and ethyl acetate.
The residue crystallizes slowly, and the crystalline product is almost wholly d-benzyl-allyl-phenyl-ammonium-d-sulphonate, the corresponding /-compound remaining as a syrupy residue.
It can also be obtained by the action of ammonia on benzyl chloride (S.
CINNAMIC ACID, or Phenylacrylic Acid, C9H80 2 or C 6 H 5 CH: CH COOH, an acid found in the form of its benzyl ester in Peru and Tolu balsams, in storax and in some gumbenzoins.
The benzyl group shows this remarkably well, since we see that phenyl is present, as is also methyl.
It may also be prepared by oxidizing benzyl alcohol with concentrated nitric acid; by distilling a mixture of calcium benzoate and calcium formate; by the condensation of chlor-oxalic ester with benzene in the presence of aluminium chloride, the ester of the ketonic acid formed being then hydrolysed and the resulting acid distilled: C 6 H 6 +Cl CO Cooc 2 H 5 = C,H5co COOC2H5d-HC1, C 6 H 5 CO 000H =C6H5CHO+C02; by the action of anhydrous hydrocyanic acid and hydrochloric acid on benzene, an aldime being formed as an intermediate product: C 6 H 6 +HCN+HC1= C6H5CH :NH HC1, Benzaldine hydrochloride C 6 H 5 CH: NH HC1+H 2 O =NH4C1+C6H5CHO; and by the action of chromium oxychloride on toluene dissolved in carbon bisulphide (A.
Technically it is prepared from toluene, by converting it into benzyl chloride, which is then heated with lead nitrate: C 6 H 5 CH 2 C1 +Pb (N03)2 = 2NO 2 +PbC1.
On the other hand, it differs from the aliphatic aldehydes in many respects; it does not form an addition product with ammonia but condenses to hydrobenzamide (C 6 H 5 CH) 3 N 2; on shaking with alcoholic potash it undergoes simultaneous oxidation and reduction, giving benzoic acid and benzyl alcohol (S.
Formaldehyde behaves abnormally with magnesium benzyl bromide (M.
Synthetically prepared by the reduction of benzoyl chloride; by the action of nitrous acid on benzylamine; by boiling benzyl chloride with an aqueous solution of potassium carbonate, or by the so-called "Cannizzaro" reaction, in which benzaldehyde is shaken up with caustic potash, one half of the aldehyde being oxidized to benzoic acid, and the other half reduced to the alcohol.
It occurs naturally in some resins, especially in gum benzoin (from Styrax benzoin), in dragon's blood, and as a benzyl ester in Peru and Tolu balsams. It can be prepared by the oxidation of toluene, benzyl alcohol, benzaldehyde and cinnamic acid; by the oxidation of benzene with manganese dioxide and concentrated sulphuric acid in the cold (L.
It may also be prepared by boiling benzyl chloride with dilute nitric acid (G.
By the action of sodium amalgam on an aqueous solution of the acid, benzyl alcohol, tetrahydrobenzoic acid and hexahydrobenzoic acid are formed.
Benzyl alcohol >>