that in the action of alcohols on diazonium salts an increase in the
molecular weight of the alcohol and an accumulation of negative groups
in the aromatic nucleus lead to a diminution in the yield of the ether
produced and to the production of a secondary reaction, resulting in
the formation of a certain amount of an aromatic hydrocarbon.

The acid esters of phenol are best obtained by the action of acid
chlorides or anhydrides on phenol or its sodium or potassium salt, or
by digesting phenol with an acid in the presence of phosphorus
oxychloride (F. Rasinski, _Jour. f. prak. Chem._, 1882 [2], 26, p.
62). Phenyl acetate, C6H5.O.COCH3, a colourless liquid of boiling
point 193 deg. C., may be prepared by heating phenol with acetamide.
When heated with aniline it yields phenol and acetanilide. Phenyl
benzoate, C6H5.O.COC5H5, prepared from phenol and benzoyl chloride,
crystallizes in monoclinic prisms, which melt at 68-69 deg. C. and
boil at 314 deg. C.

Phenol is characterized by the readiness with which it forms
substitution products; chlorine and bromine, for example, react
readily with phenol, forming ortho- and para- chlor- and -bromphenol,
and, by further action, trichlor- and tribrom-phenol. Iodphenol is
obtained by the action of iodine and iodic acid on phenol dissolved in
a dilute solution of caustic potash. Nitro-phenols are readily
obtained by the action of nitric acid on phenol. By the action of
dilute nitric acid, ortho- and para-nitrophenols are obtained, the
ortho-compound being separated from the para-compound by distillation
in a current of steam. Ortho-nitrophenol, C6H4.OH.NO2(1.2),
crystallizes in yellow needles which melt at 45 deg. C. and boil at
214 deg.C. Para-nitrophenol, C6H4.OH.NO2(1.4), crystallizes in long
colourless needles which melt at 114 deg.C. Meta-nitrophenol,
C6H4.OH.NO2.(1.3), is prepared from meta-nitraniline by diazotizing
the base and boiling the resulting diazonium salt with water. By
nitrating phenol with concentrated nitric acid, no care being taken to
keep the temperature of reaction down, trinitrophenol (picric acid) is
obtained (see PICRIC ACID). By the reduction of nitro-phenols, the
corresponding aminophenols are obtained, and of these, the meta- and
para-derivatives are the most important. Para-aminophenol,
C6H4.OH.NH2(1.4) melts at 148 deg. C., with decomposition. Its most
important derivative is phe