The Manufacture and Production of Cinnamyl-meta-cresol.
Year: 1898

page_text: Date of Application, 27th Apr., 1898
4000 Accented 25th Fab
1800
PROVISIONAL SPECIFICATION.
The Manufacture and Production of Cinnamyl-meta-cresol.
I, GEORGE WILLIAM JOHNSON, of 47, Lincoln's Inn Fields, in the County of
London, Patent Agent, do hereby declare the nature of this invention (which has
been communicated to me from abroad by Kalle & Co., of Biebrich on the Rhine,
in the Empire of Germany) to be as follows:-
Unlike the cinnamylic ethers of phenol ortho- or para-cresol, cinnamyl-meta-
cresol is of high therapeutical value.
In order to prepare this new compound according to this invention the pro-
ceeding is as follows:-
25 parts by weight of meta-cresol and 35 parts by weight of cinnamylic acid
are dissolved in 180 to 300 parts by weight of a suitable indifferent solvent (such
for instance as toluene) and to the solution so obtained 20 to 25 parts by weight
of phosphorus oxychloride are added. The solution is then heated to about 110
to 120 degrees Centigrade, until hydrochloric acid gas ceases to be evolved.
After cooling, the solution is filtered off from resinous matter formed during
the reaction. After the solvent is distilled off, the crude cinnamyl meta-cresol
remains as a feebly coloured oil, which on cooling, forms a crystalline mass.
The new body may be purified by recrystallization from alcohol. The fusion point
It is insoluble in
of the pure cinnamyl-meta-cresol is 65 degrees Centigrade.
water, but is soluble in ether, benzene, chloroform, glacial acetic acid, and hot
alcohol. The said cinnamyl-meta-cresol is obtained if, instead of the cinnamylic
acid, an equivalent quantity of cinnamylic chloride, or anhydride, be employed,
or if, instead of the phosphorus oxychloride, other suitable condensing agents be
1
employed.
The Manufacture and Production of Cinnamyl-meta-cresol.
I, GEORGE WILLIAM JOHNSON, of 47, Lincoln's Inn Fields, in the County of
London, Patent Agent, do hereby declare the nature of this invention (which has
been communicated to me from abroad by Kalle & Co., of Biebrich on the Rhine,
in the Empire of Germany) and in what manner the same is to be performed
to be particularly described and ascertained in and by the following statement:-
Unlike the cinnamylic ethers of phenol ortho-, or para-cresol, cinnamyl-meta-
val is of high theranentical value.

page_text: In order to prepare this new compound according to this invention the pro-
ceeding is as follows:-
25 parts by weight of meta-cresol and 35 parts by weight of cinnamylic acid
are dissolved in 180 to 300 parts by weight of a suitable indifferent solvent (such
for instance as toluene) and to the solution so obtained 20 to 25 parts by weight
of phosphorus oxychloride are added. The solution is then heated to about 110
to 120 degrees Centigrade, until hydrochloric acid gas ceases to be evolved.
After cooling, the solution is filtered off from resinous matter formed during
the reaction. After the solvent is distilled off, the crude cinnamyl-meta-cresol
remains as a feebly coloured oil, which on cooling, forms a crystalline mass.
The new body may be purified by recrystallization from alcohol. The fusion point
of the pure cinnamyl-meta-cresol is 65 degrees Centigrade. It is insoluble in
water, but is soluble in ether, benzene, chloroform, glacial acetic acid, and hot
alcohol. The said cinnamyl-meta-cresol is obtained if, instead of the cinnamylic
acid, an equivalent quantity of cinnamylic chloride, or anhydride be employed,
or if, instead of the phosphorus oxychloride, other suitable condensing agent be
employed.
Having now particularly described and ascertained the nature of this invention,
and in what manner the same is to be performed, I declare that what I
claim is:-
1. The manufacture of cinnamyl-meta-cresol by treating meta-cresol, in the
presence of an indifferent solvent, with cinnamylic acid, (or cinnamylic chloride,
or anhydride) and a suitable condensation agent.
2. The cinnamyl-meta-cresol produced substantially as hereinbefore described.
Dated this 17th day of January 1899.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.