US1036624A - Phenylethylmalonic ester. - Google Patents

Phenylethylmalonic ester. Download PDF

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Publication number
US1036624A
US1036624A US67447312A US1912674473A US1036624A US 1036624 A US1036624 A US 1036624A US 67447312 A US67447312 A US 67447312A US 1912674473 A US1912674473 A US 1912674473A US 1036624 A US1036624 A US 1036624A
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Prior art keywords
phenylethylmalonic
ester
esters
parts
germany
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US67447312A
Inventor
Heinrich Hoerlein
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Bayer AG
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Farbenfabriken Vorm Friedr Bayer and Co
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Priority to US67447312A priority Critical patent/US1036624A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Definitions

  • phenylethyl-malonic esters can be obtained by treating the phenylmalonie esters with ethylbromid.
  • the new esters are valuable intermediate products for the production of substituted barbituric acids which are valuable therapeutic compounds.
  • esters of'the present invention have the following general formula:
  • the phenylethylmalonic esters being liquids which are split up by the action of caustic alkali into alcohols and the phenylethylmalonic acid, substantially as descrlbed.
  • phenylethylmalonic ethyl ester being a limpid oil, boilin at 166 C. under a pressure of 12 mm.,.an' being split up by the action of caustic alkali into alcohol and the phenylethylmalonic acid, substantially as described.

Description

HEINRICH, HoBLEm,
FARBENFABRIKEN VORM. FRIEDR. BAYER & CO.,
CORPORATION 015 GERMANY.
OF VOHWINKEL, NEAR ELBERFELD, GERMANY, ASSIGNOR TO OF ELBERFELD, GERMANY, A
PHENYLETHYLMALONIC ESTER.
No Drawing.
Specification of Letters Patent. Application filed January 31, 1912. Serial No. 674,473.
Patented Aug. 27, 1912.
To all whom it may concern:
Be it known that I, HEINRICH HoRLEIN, doctor of philosophy, chemist, citizen of the German Empire, residing at Vohwinkel, near. Elberfeld, Germany, have invented new and useful Improvements in Phenylethylmalonic Esters, of which the following is a specification.
I have found that the hitherto unknown phenylethyl-malonic esters can be obtained by treating the phenylmalonie esters with ethylbromid. The new esters are valuable intermediate products for the production of substituted barbituric acids which are valuable therapeutic compounds. Upon treatment with caustic alkali they are split'up into alcohols and phenylethylmalonic acid melting at 160 C.
The esters of'the present invention have the following general formula:
CzHs 00R (Rzalkyl, aralkyl, aryl).
In order to illustrate the new process more fully the following example is given, the parts being by weight :-236 parts of phenlymalonic ester and 120 parts of ethyl-bromid (BI-C 11 are added to a solution of 23 parts of sodium in 230 parts of alcohol (free from water). The resulting mixture is then heated to boiling in a vessel provided with a reflux condenser until the liquid shows a neutral reaction to lacmus. The liquid is filtered, the alcohol is distilled off and the ester is isolated in the usual way. It is a limpid oil boiling at 166 C. under a pressure of 12 min.
I claim 1. As new products, the phenylethylmalonic esters being liquids which are split up by the action of caustic alkali into alcohols and the phenylethylmalonic acid, substantially as descrlbed.
2. The phenylethylmalonic ethyl ester, being a limpid oil, boilin at 166 C. under a pressure of 12 mm.,.an' being split up by the action of caustic alkali into alcohol and the phenylethylmalonic acid, substantially as described.
In testimony whereof I have hereunto setmy hand in the presence of two subscribing witnesses.
HEINRICH HORLEIN. [L.s.]
Witnesses HELEN NUFER, A. Nurnn.
US67447312A 1912-01-31 1912-01-31 Phenylethylmalonic ester. Expired - Lifetime US1036624A (en)

Priority Applications (1)

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US67447312A US1036624A (en) 1912-01-31 1912-01-31 Phenylethylmalonic ester.

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US67447312A US1036624A (en) 1912-01-31 1912-01-31 Phenylethylmalonic ester.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2478853A (en) * 1945-10-29 1949-08-09 Mallinckrodt Chemical Works Metallation of malonic esters
US2902509A (en) * 1956-11-23 1959-09-01 It Prodotti Schering Soc beta-diethylaminoethyl ester of ethyl alpha-phenyl-alpha-ethylmalonate and salts thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2478853A (en) * 1945-10-29 1949-08-09 Mallinckrodt Chemical Works Metallation of malonic esters
US2902509A (en) * 1956-11-23 1959-09-01 It Prodotti Schering Soc beta-diethylaminoethyl ester of ethyl alpha-phenyl-alpha-ethylmalonate and salts thereof

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