US1436304A - Benzyl ester of acetyl salicylic acid - Google Patents
Benzyl ester of acetyl salicylic acid Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- benzyl ester
- salicylic acid
- acetyl salicylic
- benzyl
- illinois
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 title description 6
- -1 Benzyl ester Chemical class 0.000 title description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FTKJKXRSODPSDE-UHFFFAOYSA-N benzyl 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 FTKJKXRSODPSDE-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US437608A US1436304A (en) | 1921-01-15 | 1921-01-15 | Benzyl ester of acetyl salicylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US437608A US1436304A (en) | 1921-01-15 | 1921-01-15 | Benzyl ester of acetyl salicylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1436304A true US1436304A (en) | 1922-11-21 |
Family
ID=23737134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US437608A Expired - Lifetime US1436304A (en) | 1921-01-15 | 1921-01-15 | Benzyl ester of acetyl salicylic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1436304A (en) |
Cited By (1)
| 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 |
-
1921
- 1921-01-15 US US437608A patent/US1436304A/en not_active Expired - Lifetime
Cited By (1)
| 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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