CA2045190A1 - Process for the synthesis of .alpha.-hydroxy-esters - Google Patents
Process for the synthesis of .alpha.-hydroxy-estersInfo
- Publication number
- CA2045190A1 CA2045190A1 CA002045190A CA2045190A CA2045190A1 CA 2045190 A1 CA2045190 A1 CA 2045190A1 CA 002045190 A CA002045190 A CA 002045190A CA 2045190 A CA2045190 A CA 2045190A CA 2045190 A1 CA2045190 A1 CA 2045190A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- synthesis
- esters
- acid
- reaction
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- -1 ester hydrochloride Chemical class 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 1
- 101100353161 Drosophila melanogaster prel gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010061926 Purulence Diseases 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/22—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02074290A IT1248983B (it) | 1990-06-22 | 1990-06-22 | Procedimento per la sintesi di alfa-idrossi esteri |
| IT20742A/90 | 1990-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2045190A1 true CA2045190A1 (en) | 1991-12-23 |
Family
ID=11171390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002045190A Abandoned CA2045190A1 (en) | 1990-06-22 | 1991-06-21 | Process for the synthesis of .alpha.-hydroxy-esters |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0463676A1 (OSRAM) |
| JP (1) | JPH04230241A (OSRAM) |
| CA (1) | CA2045190A1 (OSRAM) |
| IT (1) | IT1248983B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5066447B2 (ja) | 2005-08-08 | 2012-11-07 | 日宝化学株式会社 | ２−ヒドロキシエステル化合物の製造方法 |
| JP4822764B2 (ja) * | 2005-08-08 | 2011-11-24 | 日宝化学株式会社 | ２−ヒドロキシ−４−フェニル酪酸エチルエステルの製造方法 |
| JP5417860B2 (ja) | 2008-08-26 | 2014-02-19 | 住友化学株式会社 | α−ヒドロキシエステル類の製造方法 |
| CN102369178B (zh) | 2009-04-03 | 2015-03-11 | 三菱瓦斯化学株式会社 | α-羟基羧酸酯的制造方法 |
| WO2023169810A1 (de) | 2022-03-11 | 2023-09-14 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH125959A (de) * | 1925-09-03 | 1928-05-16 | Canadian Electro Prod Co | Verfahren zur Herstellung von Äthyllactat. |
| DE544499C (de) * | 1925-09-23 | 1932-02-18 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Milchsaeureestern |
-
1990
- 1990-06-22 IT IT02074290A patent/IT1248983B/it active IP Right Grant
-
1991
- 1991-06-14 EP EP91201487A patent/EP0463676A1/en not_active Withdrawn
- 1991-06-21 JP JP3175848A patent/JPH04230241A/ja not_active Withdrawn
- 1991-06-21 CA CA002045190A patent/CA2045190A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IT9020742A1 (it) | 1991-12-22 |
| EP0463676A1 (en) | 1992-01-02 |
| IT9020742A0 (OSRAM) | 1990-06-22 |
| JPH04230241A (ja) | 1992-08-19 |
| IT1248983B (it) | 1995-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |