CA1058218A - Method for the preparation of alpha-hydroxycarbonyl compounds - Google Patents
Method for the preparation of alpha-hydroxycarbonyl compoundsInfo
- Publication number
- CA1058218A CA1058218A CA243,382A CA243382A CA1058218A CA 1058218 A CA1058218 A CA 1058218A CA 243382 A CA243382 A CA 243382A CA 1058218 A CA1058218 A CA 1058218A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- alpha
- compounds
- osmium tetroxide
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 13
- 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 Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 230000001590 oxidative effect Effects 0.000 claims abstract description 5
- -1 alkaline earth metal chlorate Chemical class 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 238000007059 Strecker synthesis reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19167/75A IT1030968B (it) | 1975-01-10 | 1975-01-10 | Processo per la preparazione di composti alfa idrossicarbonilici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058218A true CA1058218A (en) | 1979-07-10 |
Family
ID=11155449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,382A Expired CA1058218A (en) | 1975-01-10 | 1976-01-09 | Method for the preparation of alpha-hydroxycarbonyl compounds |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS60328B2 (cs) |
| BE (1) | BE837431A (cs) |
| CA (1) | CA1058218A (cs) |
| CS (1) | CS192526B2 (cs) |
| DD (1) | DD121925A5 (cs) |
| DE (1) | DE2600657C3 (cs) |
| DK (1) | DK7876A (cs) |
| FR (1) | FR2297199A1 (cs) |
| GB (1) | GB1510051A (cs) |
| HU (1) | HU174633B (cs) |
| IL (1) | IL48771A (cs) |
| IT (1) | IT1030968B (cs) |
| LU (1) | LU74143A1 (cs) |
| NL (1) | NL162889C (cs) |
| NO (1) | NO147241C (cs) |
| SE (1) | SE427270B (cs) |
| YU (1) | YU4276A (cs) |
| ZA (1) | ZA7646B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142426U (cs) * | 1989-05-06 | 1990-12-03 | ||
| EP0482834B1 (en) * | 1990-10-20 | 1996-01-17 | Takasago International Corporation | Process for producing alpha-hydroxyketones |
| JP2017043835A (ja) | 2015-08-25 | 2017-03-02 | 株式会社神戸製鋼所 | 冷間加工用機械構造用鋼、およびその製造方法 |
-
1975
- 1975-01-10 IT IT19167/75A patent/IT1030968B/it active
- 1975-12-31 IL IL48771A patent/IL48771A/xx unknown
-
1976
- 1976-01-05 ZA ZA00760046A patent/ZA7646B/xx unknown
- 1976-01-06 GB GB385/76A patent/GB1510051A/en not_active Expired
- 1976-01-07 CS CS76101A patent/CS192526B2/cs unknown
- 1976-01-08 LU LU74143A patent/LU74143A1/xx unknown
- 1976-01-08 FR FR7600337A patent/FR2297199A1/fr active Granted
- 1976-01-08 DD DD190736A patent/DD121925A5/xx unknown
- 1976-01-08 NO NO760050A patent/NO147241C/no unknown
- 1976-01-09 YU YU00042/76A patent/YU4276A/xx unknown
- 1976-01-09 JP JP51001662A patent/JPS60328B2/ja not_active Expired
- 1976-01-09 BE BE163402A patent/BE837431A/xx not_active IP Right Cessation
- 1976-01-09 SE SE7600179A patent/SE427270B/xx unknown
- 1976-01-09 DK DK7876*#A patent/DK7876A/da not_active Application Discontinuation
- 1976-01-09 DE DE2600657A patent/DE2600657C3/de not_active Expired
- 1976-01-09 CA CA243,382A patent/CA1058218A/en not_active Expired
- 1976-01-09 NL NL7600225.A patent/NL162889C/xx not_active IP Right Cessation
- 1976-01-09 HU HU76SA2876A patent/HU174633B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO147241C (no) | 1983-03-09 |
| IL48771A0 (en) | 1976-02-29 |
| NL7600225A (nl) | 1976-07-13 |
| AU1000676A (en) | 1977-07-14 |
| FR2297199A1 (fr) | 1976-08-06 |
| DE2600657A1 (de) | 1976-07-15 |
| NO760050L (cs) | 1976-07-13 |
| DE2600657B2 (de) | 1979-11-22 |
| IT1030968B (it) | 1979-04-10 |
| SE7600179L (sv) | 1976-07-12 |
| LU74143A1 (cs) | 1976-07-20 |
| NL162889C (nl) | 1980-07-15 |
| CS192526B2 (en) | 1979-08-31 |
| DD121925A5 (cs) | 1976-09-05 |
| IL48771A (en) | 1979-01-31 |
| DK7876A (da) | 1976-07-11 |
| YU4276A (en) | 1982-02-28 |
| JPS60328B2 (ja) | 1985-01-07 |
| ZA7646B (en) | 1976-12-29 |
| BE837431A (fr) | 1976-07-09 |
| HU174633B (hu) | 1980-02-28 |
| GB1510051A (en) | 1978-05-10 |
| FR2297199B1 (cs) | 1980-05-30 |
| JPS5195009A (cs) | 1976-08-20 |
| DE2600657C3 (de) | 1980-07-24 |
| NL162889B (nl) | 1980-02-15 |
| SE427270B (sv) | 1983-03-21 |
| NO147241B (no) | 1982-11-22 |
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