Production of Ethylether of Cinnamic Acid.
Year: 1890

page_text: Date of Application, 29th Mar., 1890
Complete Specification Left, 15th Dec., 1890-Accepted, 21st Feb.; 1891
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE FARBWERKE VORMALS MEISTER LUCIUS
AND BRUNING, of Hoechst */ Main, Germany.]
Production of Ethylether of Cinnamic Acid.
I, OLIVER IMRAY, of No. 28, Southampton Buildings, Chancery Lane, in the
County of London, Fellow of the Institute of Patent Agents, do hereby declare
the nature of this invention to be as follows:-
:-
The only way of producing the ethylether of cinnamic acid hitherto known is
etherising the cinnamic acid.
According to the process of my foreign correspondents, the ethylether of cinnamic
acid can be directly produced from benzaldehyde without its being necessary
previously to insulate the cinnamic acid, by the action of benzaldehyde upon acetic
ether in which is suspended some metallic sodium.
The reaction goes on easily and smoothly and as only a small quantity of sodium
is used in this process for the production of the ethylether of cinnamic acid, its
production in this way is more advantageous than by the processes hitherto
known.
The best way for producing nitro cinnamic acid being by nitrating the ethylether
of the cinnamic acid and not the cinnamic acid itself, this process can be considered
a notable simplification of the synthesis of the ortho-nitrophenylpropiolic acid or of
the indigo.
The invention is carried out in the following way:
To acetic ether (free of alcohol) (about 5 to 6 molecules) kept cool by means of
iced water, is added sodium in small pieces. To this is caused to flow benzaldehyde
in such way that the reaction never becomes too brisk.
When the whole quantity of metallic sodium has disappeared, there is added such
quantity of acetic acid, as corresponds to the quantity of sodium used.
By diluting with water, the ether is separated, the oily layer taken off, dried with
chloride of calcium, the acetic ether is distilled off from the water bath and the
ether is rectified.
It distils completely at about 260 to 275° C.
Dated this 20th day of Mar 1900
COMPLETE SPECIFICATION.
Production of Ethylether of Cinnamic Acid.
I, OLIVER IMKAY, of No. 28, Southampton Buildings, Chancery Lane, in the
County of London, Fellow of the Institute of Patent Agents, do hereby declare
the nature of this invention and in what manner the same is to be performed to be
particularly described and ascertained in and by the following statement :-
The only way of producing the ethylether of cinnamic acid hitherto known is
etherising the cinnamic acid.
According to the process of my foreign correspondents, the ethylether of cinnamic
acid can be directly produced from benzaldehyde without its being necessary
previously to insulate the cinnamic acid, by the action of benzaldehyde upon acetic
ether in which is suspended some metallic sodium.
The reaction goes on easily and smoothly and as only a small quantity of sodium
is used in this process for the production of the ethylether of cinnamic acid, its
ונגמ

page_text: production in this way is more advantageous than by the processes hitherto
known.
The best way for producing nitro cinnamic acid being by nitrating the ethylether
of the cinnamic acid and not the cinnamic acid itself, this process can be con-
sidered a notable simplification of the synthesis of the ortho-nitrophenylpropiolic
acid or of the indigo.
The invention is carried out in the following way:
To 45 parts by weight of acetic ether (free of alcohol) kept cool by means of
iced water, is added 1-15 parts of sodium in small pieces. To this is caused to flow
benzaldehyde 10-65 parts by weight in such way that the reaction never becomes
too brisk.
When the whole quantity of metallic sodium has disappeared, there is added
such quantity of acetic acid, as corresponds to the quantity of sodium used.
By diluting with water, the ether is separated, the oily layer taken off, dried
with chloride of calcium, the acetic ether is distilled off from the water bath
and the ether is rectified. It distils completely at about 260 to 275° C.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
:―
1. The production of ethylether of cinnamic acid by the action of benzaldehyde
upon acetic ether in the presence of metallic sodium, substantially as herein
described.
2. The ethylether of cinnamic acid produced as above set forth.
ABEL & IMRAY,
Agents for the Applicant.