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NITRO DERIVATIVES OF HALOGENOBENZENES 461

TABLE 104

SOLUBILITY OF PICRYL CHLORIDE IN ORGANIC SOLVENTS

(g/100 g OF SOLVENT)

Solvent

Methyl alcohol

Ethyl alcohol (absolute)

Ether

Ethyl acetate

Acetone

Chloroform

Carbon tetrachloride

Benzene

Toluene

* At 31°C.

at 17°C at 50°C

10.24

4.48

7.23

91.5

212.0

12.36

0.56

36.39

89.44

34.8

15.1

10.6*

238.35

546.4

233.4

2.45

428.1

321.1

Chemical properties. The chlorine atom in a picryl chloride molecule is excep-

tionally reactive. Besides hydrolysis to picric acid when heated with water, as men-

tioned above, picryl chloride can yield picric acid when boiled with alcohols, accord-

ing to the equation:

(7)

If the reaction proceeds in the presence of sodium, potassium or calcium hydroxides,

the corresponding picric acid ethers are formed:

(8)

The same compounds can be obtained by the action of the corresponding alcohol-

ates, through the formation of intermediate addition products:

(9)