US1436304A - Benzyl ester of acetyl salicylic acid - Google Patents

Benzyl ester of acetyl salicylic acid Download PDF

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Publication number
US1436304A
US1436304A US437608A US43760821A US1436304A US 1436304 A US1436304 A US 1436304A US 437608 A US437608 A US 437608A US 43760821 A US43760821 A US 43760821A US 1436304 A US1436304 A US 1436304A
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Prior art keywords
benzyl ester
salicylic acid
acetyl salicylic
benzyl
illinois
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US437608A
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Alfred S Burdick
Elmer B Vliet
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Abbott Laboratories
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Abbott Laboratories
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/90—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl and carboxyl groups

Definitions

  • the object of our invention is to provide an improved compound for internal medication, which shall have pronounced antispasinodic properties in addition to the wellknown medicinal qualities possessed by aspirin, i. e. acetylsalicylic acid.
  • Preparation-Benzyl salicylate (1 mol.) is mixed with acetic anhydride (1;, mol.) and anhydrous sodium acetate mol.) and heated in an oil bath at 140 C. for 2 hours.
  • benzyl ester of acetylsalicylic acid is a white solid melting at 25.526 (l, which upon melting gives a straw colored, rather viscous liquid which has an index of refraction of 92% 1.5540.
  • Benzyl acetylsalicylate is very soluble in carbon tetrachloride, benzene, xylene, ethyl acetate and acetone but is only slightly soluhle in petroleum ether. 0

Description

Patented Nov. 21, 1922.
ET YATES l iidd ii ALFRED S. BURDIOK AND ELIVIER B. VLIET, OF CHICAGO, ILLINOIS, ASSIGNORS TO THE ABBOTT LABORATORIES, OF CHICAGO, ILLINOIS, A CORPORATION OF ILLINOIS.
IBENZYL ESTER OF ACETYL SALIOYLIC ACID.
N Drawing.
. To all whom it may concern:
Be it known that we, ALFRED S. BURDIGK and ELMER B. VLIET, both citizens of the United States, residing at Chicago, in the county of Cook and State of Illinois, have invented certain new and useful Improvements in Benzyl Ester of Acetyl Salicylic Acid, of which the following is a specification.
The object of our invention is to provide an improved compound for internal medication, which shall have pronounced antispasinodic properties in addition to the wellknown medicinal qualities possessed by aspirin, i. e. acetylsalicylic acid.
Preparation-Benzyl salicylate (1 mol.) is mixed with acetic anhydride (1;, mol.) and anhydrous sodium acetate mol.) and heated in an oil bath at 140 C. for 2 hours.
Upon cooling, the solution solidifies. This is brought into solution by triturating with benzene and water. The benzene solution is dried and distilled. The fraction distilling between 170200 C. at 5 min. pressure is collected. Upon long standing in an ice bath this solidifies and pure benzyl acetylsalicylate is obtained from this by several Serial No. 437,608.
crystallizations from a mixture of petroleum ether and carbon tetrachloride.
P1 0perties.The benzyl ester of acetylsalicylic acid is a white solid melting at 25.526 (l, which upon melting gives a straw colored, rather viscous liquid which has an index of refraction of 92% 1.5540.
Analysis.
0.1347 gms. substance0.3505 gins. CO 0.06414: gins. H O.
O l-l U Theory :C7 1.08% l-l5.22% Found 70.96% 5.35%
Benzyl acetylsalicylate is very soluble in carbon tetrachloride, benzene, xylene, ethyl acetate and acetone but is only slightly soluhle in petroleum ether. 0
Clinical tests indicate that this compound is an efiicient anti-spasn1odic in addition to having well-known desirable medicinal properties of acetylsalicylic acid.
Vi e claim as our invention:
The benzyl ester of acetylsalicylic acid.
ALFRED S. BURDICK. ELMER B. VLIET.
US437608A 1921-01-15 1921-01-15 Benzyl ester of acetyl salicylic acid Expired - Lifetime US1436304A (en)

Priority Applications (1)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199576A (en) * 1976-12-15 1980-04-22 The Procter & Gamble Company Analgesic and anti-inflammatory compositions for topical application

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199576A (en) * 1976-12-15 1980-04-22 The Procter & Gamble Company Analgesic and anti-inflammatory compositions for topical application

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