DE235357C - - Google Patents
Info
- Publication number
- DE235357C DE235357C DENDAT235357D DE235357DA DE235357C DE 235357 C DE235357 C DE 235357C DE NDAT235357 D DENDAT235357 D DE NDAT235357D DE 235357D A DE235357D A DE 235357DA DE 235357 C DE235357 C DE 235357C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- cinnamic acid
- heated
- ether
- acid
- 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.)
- Active
Links
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 11
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 11
- 229930016911 cinnamic acid Natural products 0.000 claims description 11
- 235000013985 cinnamic acid Nutrition 0.000 claims description 11
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- 239000004857 Balsam Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000018716 Impatiens biflora Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- 101100493705 Caenorhabditis elegans bath-36 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000014150 Myroxylon pereirae Nutrition 0.000 description 1
- 244000302151 Myroxylon pereirae Species 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- NGHOLYJTSCBCGC-VAWYXSNFSA-N benzyl cinnamate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-VAWYXSNFSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NGHOLYJTSCBCGC-UHFFFAOYSA-N cis-cinnamic acid benzyl ester Natural products C=1C=CC=CC=1C=CC(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE235357C true DE235357C (enExample) |
Family
ID=495140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT235357D Active DE235357C (enExample) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE235357C (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006047466A3 (en) * | 2004-10-21 | 2006-09-21 | Univ Duke | Ophthamological drugs |
| WO2007127639A3 (en) * | 2006-04-26 | 2008-06-12 | Aerie Pharmaceuticals Inc | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
-
0
- DE DENDAT235357D patent/DE235357C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006047466A3 (en) * | 2004-10-21 | 2006-09-21 | Univ Duke | Ophthamological drugs |
| US8642644B2 (en) | 2004-10-21 | 2014-02-04 | Duke University | Ophthamological drugs |
| WO2007127639A3 (en) * | 2006-04-26 | 2008-06-12 | Aerie Pharmaceuticals Inc | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1468529B2 (de) | Rechtsdrehendes !,S-Dioxo^-ir-carboxyäthyl)-7aß-methyl-5,6,7,7a-tetrahydroindan und Verfahren zu seiner Her- | |
| DE235357C (enExample) | ||
| DE1205102B (de) | Verfahren zur Herstellung von 4-[2'-(beta-Morpholinoaethoxycarbonyl)-phenylamino]-7-corchinolin | |
| DE1468890B1 (de) | Verfahren zur Herstellung von Tetrahydroindan-Zwischenprodukten fuer Steroidderivate | |
| DE574838C (de) | Verfahren zur Darstellung von cyclischen Glykolen und ihren Derivaten bzw. von Ketonen | |
| DE1249263B (de) | Verfah ren zur Herstellung vor substituierten 1,3 Dioxocyclopentanderivaten | |
| DE2209372C2 (de) | 3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als Riechstoff | |
| DE875359C (de) | Verfahren zur Darstellung von Pantothensaeure | |
| DE838140C (de) | Verfahren zur Herstellung von Amiino-aryl-pyridlyl-alkanolen und ihren Estern | |
| DE1118197B (de) | Verfahren zur Herstellung von 6-Azasterinen | |
| DE164128C (enExample) | ||
| DE721180C (de) | Verfahren zur Herstellung von fluorierten aliphatischen Verbindungen | |
| DE657055C (de) | Verfahren zur Darstellung von hoeher molekularen Verbindungen | |
| DE974692C (de) | Verfahren zur Herstellung von 2, 2-disubstituierten 5-Acylamino-4-(p-nitrophenyl)-1,3-dioxanen | |
| DE1151794B (de) | Verfahren zur Herstellung des Mononatriumsalzes der Phospho-enolbrenztraubensaeure | |
| DE901415C (de) | Verfahren zur Herstellung von í¸-Androstadienol-(17)-on-(3) bzw. seiner funktionellen Derivate der Hydroxylgruppe | |
| DE872044C (de) | Verfahren zur Herstellung von Verbindungen von Sexualhormonen | |
| DE527715C (de) | Verfahren zur Darstellung leicht loeslicher Salze der 3-Acetylamino-4-oxybenzol-1-arsinsaeure | |
| DE2238260C3 (de) | Phosphorsäuremonoester von 5-(2-Dimethylaminoäthoxy)-carvacrol, Verfahren zu seiner Herstellung und diesen enthaltende Arzneimittel | |
| DE893795C (de) | Verfahren zur Herstellung von neuen Thiolverbindungen | |
| DE1493658C (de) | Verfahren zur Herstellung von Hydroxy aminosauretert butylathern und ihren N Carbonbenzoxyverbindungen | |
| AT205962B (de) | Verfahren zur Herstellung von neuen ungesättigten aliphatischen Amino-diolen | |
| DE920076C (de) | Verfahren zur Herstellung von kernalkylierten 2, 4, 6-Trioxybenzoesaeureestern | |
| DE1468531C2 (de) | Rechtsdrehende Hexahydroindanpropionsäurederivate und Verfahren zu ihrer Herstellung | |
| DE2935749A1 (de) | 4-methyl-2,5-dioxa-bicyclo (4.4.0) decan-3-on, dessen herstellung und verwendung als riechstoff sowie dieses enthaltende riechstoffkompositionen |