US509520A - Paul fritsch - Google Patents
Paul fritsch Download PDFInfo
- Publication number
- US509520A US509520A US509520DA US509520A US 509520 A US509520 A US 509520A US 509520D A US509520D A US 509520DA US 509520 A US509520 A US 509520A
- Authority
- US
- United States
- Prior art keywords
- paul
- ester
- fritsch
- acetol
- salicylic
- 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
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 10
- 150000003902 salicylic acid esters Chemical class 0.000 description 10
- BULLHNJGPPOUOX-UHFFFAOYSA-N Chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 8
- 229960001860 salicylate Drugs 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- -1 and mon-iodoacetone Chemical compound 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VQFAIAKCILWQPZ-UHFFFAOYSA-N Bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- 231100000614 Poison Toxicity 0.000 description 2
- 206010072736 Rheumatic disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000000249 desinfective Effects 0.000 description 2
- 201000008286 diarrhea Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000035943 smell Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002485 urinary Effects 0.000 description 2
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
- C07C69/88—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 carboxyl groups
Definitions
- esters of this acetol which latter is also known as acetone-alcohol, acetylcarbinol and pyruvyl alcohol
- acetic-acid-ester and benzoicacid-ester have heretofore been produced.
- the former has been produced by Henry (Bem'chte der Deutschen Chemischenmaschine, V, 966) and the latter has been produced by Breuer dz Fincke (Bcrichte dc-r Deutschen C'hcmz'schenmaschine, XIII, 639).
- the last named chemists obtained from eighty grams of monochloracetone only fifty grams of benzoylacetol.
- the operation may conveniently be carried out in the following manner: Over about one hundred and eighty parts by weight of salicylate of soda are poured about two hundred parts by weight of spirit; then about 92.5 parts by weight of monochloracetone are added thereto, and the mixture heated on a reflux cooler until the pungent smell of the mouochloracetone has disappeared.
- the spirit is then distilled off and the product of the reaction is poured while still warm, into a dilute solution of soda.
- the new ester is separated as a heavy oil that solidifies after a short. time.
- the ester is purified by recrystallization from spirit in which it is readily soluble by the aid of heat, but in which itis only soluble with difficulty in a cold state.
- the reaction will also take place when the components are heated in an aqueous or aqueous-alcoholic solution and also but with a less yield when the components are heated together without solvents.
- the salicylic-acid-ester of acetol produced according to this invention is suitable for use as a medicine for diarrhea and gouty rheumatism and for the disinfection of the urinary passages.
- the dose is from a half gram to three grams daily according to the age of the patient.
Description
" UNTTED STATES PATENT OFFICE.
PAUL FRITSOH, OF MARBURG, GERMANY.
SALICYLIC ESTER OF ACETOL.
SPECIFICATION forming part of Letters Patent No. 509,520, dated November 28, 1893.
Application filed July 5, 1893- Serial No. 479.640. ($pecimens.) Patented in Germany September 9, 1892. lie- 70,054; in France January 6,1893, No. 226,951, and in Belgium February 28, 1893, lie-103,519.
To aZZ whom it rat-cry concern:
Be it known that I, PAUL FRITSCH, chemist, of Marburg, in the Province of Hesse-Nassau, in the Kingdom of Prussia, Germany, have invented certain new and useful Improvements in Salicylic-Acid Ester of Acetol, of which the following is a specification, and for which I salicylic acid is combined with a non-poisonous substance. According thereto I have produced an ether of this kind by the reaction upon each other of monochlorace tone and salicylate of soda. Upon the separation of the resulting sodium chloride, the salicylicacid-ester of acetol is obtained. Of the esters of this acetol (which latter is also known as acetone-alcohol, acetylcarbinol and pyruvyl alcohol) only acetic-acid-ester and benzoicacid-ester have heretofore been produced. The former has been produced by Henry (Bem'chte der Deutschen Chemischen Gesellschaft, V, 966) and the latter has been produced by Breuer dz Fincke (Bcrichte dc-r Deutschen C'hcmz'schen Gesellschaft, XIII, 639). The last named chemists obtained from eighty grams of monochloracetone only fifty grams of benzoylacetol. Now I have discovered that by causing a reaction between a mono-halogen acetone such as monochloracetone, monobrom-acetone, and mon-iodoacetone, and a salicylate such as salicylate of soda, which reaction takes place almost quantitatively, salicylic-acidester of acetol can be produced. This reaction may be caused to take place by heating, the components with or withoutsolvents.
The operation may conveniently be carried out in the following manner: Over about one hundred and eighty parts by weight of salicylate of soda are poured about two hundred parts by weight of spirit; then about 92.5 parts by weight of monochloracetone are added thereto, and the mixture heated on a reflux cooler until the pungent smell of the mouochloracetone has disappeared. The spirit is then distilled off and the product of the reaction is poured while still warm, into a dilute solution of soda. The new ester is separated as a heavy oil that solidifies after a short. time. The ester is purified by recrystallization from spirit in which it is readily soluble by the aid of heat, but in which itis only soluble with difficulty in a cold state. The reaction will also take place when the components are heated in an aqueous or aqueous-alcoholic solution and also but with a less yield when the components are heated together without solvents.
The salicylic-acid-ester of acetol, produced according to the following equation:
NaCl+O H,
crystallizes from spirit in long woolly needles and melts at 71 centigrade. It is insoluble in cold water, soluble only with great difliculty in hot water, easily soluble in warm alcohol, in ether, carbon, disnlfid, chloroform and benzine, and soluble only with difficulty in cold alcohol and in ligroin. By letting it stand for a short time with ammonia or dilute solution of soda it is saponified with great facility.
The salicylic-acid-ester of acetol produced according to this invention is suitable for use as a medicine for diarrhea and gouty rheumatism and for the disinfection of the urinary passages. The dose is from a half gram to three grams daily according to the age of the patient.
In testimony that I claim the foregoing as my invention I have signed my name in presence of two subscribing witnesses.
PAUL FRITSCH.
\Vitnesses:
FRIEDE BocKqL, FERDINAND ROLLER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US509520A true US509520A (en) | 1893-11-28 |
Family
ID=2578349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US509520D Expired - Lifetime US509520A (en) | Paul fritsch |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US509520A (en) |
-
0
- US US509520D patent/US509520A/en not_active Expired - Lifetime
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