CA1108178A - Process for preparing alpha-oxoesters - Google Patents
Process for preparing alpha-oxoestersInfo
- Publication number
- CA1108178A CA1108178A CA286,454A CA286454A CA1108178A CA 1108178 A CA1108178 A CA 1108178A CA 286454 A CA286454 A CA 286454A CA 1108178 A CA1108178 A CA 1108178A
- Authority
- CA
- Canada
- Prior art keywords
- oxoesters
- preparing alpha
- acetylenic compound
- osmium tetroxide
- alpha
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000012285 osmium tetroxide Substances 0.000 claims abstract description 16
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 16
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- YHYKAMJEIQTQCW-UHFFFAOYSA-N sulfanylideneosmium Chemical compound [Os]=S YHYKAMJEIQTQCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- 229940035423 ethyl ether Drugs 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 3
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 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
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000004716 alpha keto acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- -1 methyl alpha-ketobutyrate Chemical compound 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003568 thioethers Chemical class 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
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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 |
|---|---|---|---|
| IT28041/76A IT1077057B (it) | 1976-10-06 | 1976-10-06 | Processo per la preparazione di alfa-ossoesteri |
| IT28041A/76 | 1976-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108178A true CA1108178A (en) | 1981-09-01 |
Family
ID=11222803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA286,454A Expired CA1108178A (en) | 1976-10-06 | 1977-09-09 | Process for preparing alpha-oxoesters |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5851892A (ja) * | 1981-09-24 | 1983-03-26 | Eisai Co Ltd | 粗エラスタ−ゼの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048622A (en) * | 1960-12-16 | 1962-08-07 | Union Carbide Corp | Preparation of alpha-ketoesters |
| US3065259A (en) * | 1961-02-27 | 1962-11-20 | Merck & Co Inc | Method of making alpha-diketones |
-
1976
- 1976-10-06 IT IT28041/76A patent/IT1077057B/it active
-
1977
- 1977-09-09 CA CA286,454A patent/CA1108178A/en not_active Expired
- 1977-09-16 GB GB38822/77A patent/GB1553330A/en not_active Expired
- 1977-09-20 FR FR7728242A patent/FR2367047A1/fr active Granted
- 1977-10-03 JP JP11796577A patent/JPS5346919A/ja active Pending
- 1977-10-05 DE DE2744828A patent/DE2744828C3/de not_active Expired
- 1977-10-05 LU LU78257A patent/LU78257A1/xx unknown
- 1977-10-06 NL NL7710999A patent/NL7710999A/xx not_active Application Discontinuation
- 1977-10-06 BE BE181507A patent/BE859443A/xx not_active IP Right Cessation
- 1977-10-06 CH CH1224977A patent/CH625200A5/it not_active IP Right Cessation
-
1979
- 1979-04-24 US US06/033,014 patent/US4232169A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2744828B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-06-21 |
| GB1553330A (en) | 1979-09-26 |
| IT1077057B (it) | 1985-04-27 |
| BE859443A (fr) | 1978-04-06 |
| DE2744828C3 (de) | 1980-02-14 |
| FR2367047B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-10-22 |
| DE2744828A1 (de) | 1978-04-13 |
| NL7710999A (nl) | 1978-04-10 |
| LU78257A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-26 |
| JPS5346919A (en) | 1978-04-27 |
| CH625200A5 (en) | 1981-09-15 |
| US4232169A (en) | 1980-11-04 |
| FR2367047A1 (fr) | 1978-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |