This section is from the book "Alcohol, Its Production, Properties, Chemistry, And Industrial Applications", by Charles Simmonds. Also available from Amazon: Alcohol: Its Production, Properties, Chemistry, And Industrial Applications.
A somewhat similar reaction to the foregoing has been used by Blanksma.2 By the action of sodium ethylate on l-chloro-2:4-dinitrobenzene the compound 2: 4-dinitrophenetole is obtained: -
C6H3(NO2)2C1 + C2H5.ONa = C6H3(NO2)2.O.C2H5 + NaCl.
The alcohol is concentrated to a strength of 90-95 per cent., and 05 gram taken. In this is dissolved 0012 gram of sodium, and 0 1 gram of the powdered chlorodinitrobenzene added. On warming the mixture, needles of the dinitrophenetole are obtained, which may be recrystallised from dilute alcohol or benzene, and the identity of the compound established by its melting point (85.2°). Methyl alcohol similarly treated yields 2: 4-dinitroanisole, melting at 86.9°. As the difference between these melting-points is small, the process must evidently be used with circumspection, Mixtures of the two products, containing respectively 20.5, 46 2, and 80.5 per cent. of the phenetole, have the melting points 76°, 53°, and 75°.
 
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