Improvements in the Manufacture of Alkyl-ethers from Acetyl and similar Derivatives of p-amido-phenols.
Year: 1894

page_text: 1. 1
Date of Application, 9th Oct., 1894
Complete Specification Left, 9th July, 1895-Accepted, 10th Aug.;- 1895' ****.
F. }
PROVISIONAL SPECIFICATION.
14
Improvements in the Manufacture of Alkyl-ethers from Acetyl and
similar Derivatives of p-amido-phenols....
す
...
.
1
**
I; JAMES YATE JOHNSON of 47 Lincoln's Inn. Fields in the County of London,
Gentleman, do hereby declare the nature of this invention (which has been
communicated to me from abroad by C. F. Boehringer and Soobne of Waldhof
near Mannheim in the Empire of Germany) to be as follows:-
In order to produce alkyl-ethers from acetyl and similar derivatives of p-amido-
phenols, it has hitherto been necessary to start with an alkyl-ether of a given
p-amido-phenol and 'to introduce into the latter the' remnant of acid..
i
Now we have found that free p-amido-phenol itself may be employed as the
initial substance' or body in starting the operation. For this purpose the proper
derivate of that chemical is first obtained, by treatment with acetyl. or the like
derivatives in the presence of nitrogen, when it will be found capable of being
converted without any difficulty into its alkyl-ethers by tho. well known methods.
To produce acetyl-p-phenetidine, for example; the operation to be performed is
as follows but I do not limit myself to the precise details given:
1
151 parts by weight of acetyl-p-amido-phenol, melting at 179° Centigrade, are
dissolved in a four or five times larger quantity of pure or rectified spirit of wine
and heated with 5 parts by weight. of caustic soda at 80 per cent. and 10:9 parts by
weight of bromide of aethyl to a temperature of from 100 to 110° Centigrade in a
digester for a number of hours. When the reaction has taken place, the alcohol is
distilled off and the residue boiled in water with the addition of carbon.
:
The product, as it cools down, yields a liberal percentage of crystallized acetyl-
p-phenetidine, melting at 135° Centigrade.
be
To obtain the required 'aethyls (or ethers), combinations of aethyl with chlorine,
iodine, sulphate of potassium or any other well known aethylizing medium may,
employed.
To produce lactyl-p-phenetidine, the operation is carried out in a similar manner,
lactyl-p-amido-phenol being treated with an alkali and with halogen-alkyl.
The lactyl-p-amido-phenol, which has not hitherto been described or defined,
forms colourless crystals melting at 140° Centigrade and readily soluble in hot
water and alcohol, while it will only dissolve with difficulty in ether, benzol,
chloroform and ligroin; and it is obtained by heating' p-amido-phenol for a
lengthy period of time with the admixture of a slightly more than equi-molecular
quantity of lactic acid to a temperature of 140° in an open vessel!
The method just described, for producing alkyl ethers, from acetyl and similar
derivatives of p-amido-phenols offers this advantage over the methods employed
hitherto, that the acylizing operation, in the course of which a considerable
quantity of colouring matter is always formed, here takes place at an earlier period,
or in an earlier stage of the process, which circumstance, materially facilitates the
purification of the final product.
i
I
Th
01004
1

page_text: Improvements in the Manufacture of Alkyl-ethers from Acetyl and
similar Derivatives of Para-amido-phenols.
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of London,.
Gentleman, do hereby declare the nature of this invention (which has been com
municated to me from abroad by C. E. Boehringer and Sochne of Waldhof near
Mannheim 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:
'In order to produce alkylethera from acetyl and similar derivatives of para-
amido-phenols, it has hitherto been necessary to start with an alkyl ether of a
given para-amido-phenol and to introduce into the batter the remnant of acid.
My foreigon correspondents have found that free para-amido-phenol itself-may
be employed as the initial substance, or body, in starting the operation. For this
purpose the proper derivative of that chemical is first obtained by .treatment with
acetyl or the like in the presence of nitrogen, when it will be found capable of
being converted without any difficulty into its alkyl-ethers. by the well known
methods.
To produce acetyl-para-phenetidine, for example, the operation to be performed
is as follows; (but I do not limit myself to the precise details given).
15.1 parts by-weight of acetyl-para-amido-phenol, melting at 179° Centigrade
are dissolved in a four or five times larger quantity of pure or reotified spirits of
wine and heated with 5 parts by weight of caustic soda solution of.80 per cent.
and 109 parts by weight of bromide of aethyl to a temperature: of from 100°
to 110 Centigrade in a digester for a number of hours. When the reaction has
taken place, the alcohol is distilled off, and the residue boiled in water with .the
addition of carbou.
.The product, as it cools down, yields a liberal,percentage of crystallized acetyl-
para-phenetidine, melting at 135° Centigrade.
To obtain the required aethyls (or ethers) combinations of aethyl with chlorine,
iodine, sulphate of potassium or any other well known aethylizing medium may be
employed:
To produce lactyl-para-phenetidine, the operation is carried out in a similar
manner, lactyl-para-amido-phenol being treated with an alkali and with halogen-
alkyl.
The lactyl-para-amido-phenol, which has not hitherto been described or defined,
forms: colourless crystals melting at 140° Centigrade and readily soluble in hot
water and alcohol but it will dissolve only with difficulty in.ether, bouzol, chloroform
and ligroin; and it is obtained by heating para-amido-phenol for a considerable
period of time with the admixture of a slightly more than equi-molecular quantity
of laetic acid to a temperature of 140° in an open vessel.
•
The method just described, for producing alkyl-ethers from acetyl and similar
derivatives of para-amido-phenols, offers the advantage over the methods employed
hitherto, that the acylizing operation (in the course of which a considerable
quantity of colouring matter is always formed) here takes place at an earlier period,
or in an earlier stage of the process; which circumstance materially facilitates the
purification of the final product.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed I declare that what
olaim is
In the manufacture of alkyl-ethers from acetyl or similar derivatives of para-

page_text: amido-phenols the preliminary, or preparatory, introduction of an acid remnant
into the para-amido-phenol and the subsequent alkylizing of the acetyl or similar
derivative of para-amido-phenol.
D
03T_1_ 100%
JOHNSONS & WILLCOX,
Agents.