JPH0129782B2 - - Google Patents
Info
- Publication number
- JPH0129782B2 JPH0129782B2 JP55096333A JP9633380A JPH0129782B2 JP H0129782 B2 JPH0129782 B2 JP H0129782B2 JP 55096333 A JP55096333 A JP 55096333A JP 9633380 A JP9633380 A JP 9633380A JP H0129782 B2 JPH0129782 B2 JP H0129782B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- substituted
- acid
- water
- oxo
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 50
- -1 malonic acid diester Chemical class 0.000 claims description 21
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- ROZSFNKSMIZYLM-UHFFFAOYSA-N dimethyl 2-(3-oxo-2-pentylcyclopentyl)propanedioate Chemical compound CCCCCC1C(C(C(=O)OC)C(=O)OC)CCC1=O ROZSFNKSMIZYLM-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000002168 ethanoic acid esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- YZKUNNFZLUCEET-RMKNXTFCSA-N (2e)-2-pentylidenecyclopentan-1-one Chemical compound CCCC\C=C1/CCCC1=O YZKUNNFZLUCEET-RMKNXTFCSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- YZKUNNFZLUCEET-UHFFFAOYSA-N 2-pentylidenecyclopentan-1-one Chemical compound CCCCC=C1CCCC1=O YZKUNNFZLUCEET-UHFFFAOYSA-N 0.000 description 1
- PQEYTAGBXNEUQL-UHFFFAOYSA-N 9,10-Dihydrojasmonic acid Chemical compound CCCCCC1C(CC(O)=O)CCC1=O PQEYTAGBXNEUQL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000005188 oxoalkyl group Chemical group 0.000 description 1
- 210000001177 vas deferen Anatomy 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9633380A JPS5721340A (en) | 1980-07-15 | 1980-07-15 | Continuous preparation of substituted acetic ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9633380A JPS5721340A (en) | 1980-07-15 | 1980-07-15 | Continuous preparation of substituted acetic ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5721340A JPS5721340A (en) | 1982-02-04 |
| JPH0129782B2 true JPH0129782B2 (de) | 1989-06-14 |
Family
ID=14162080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9633380A Granted JPS5721340A (en) | 1980-07-15 | 1980-07-15 | Continuous preparation of substituted acetic ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5721340A (de) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312842A (en) * | 1976-07-16 | 1978-02-04 | Roure Bertrand Dupont Sa | Process for preparing cycloalkyl compound |
-
1980
- 1980-07-15 JP JP9633380A patent/JPS5721340A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312842A (en) * | 1976-07-16 | 1978-02-04 | Roure Bertrand Dupont Sa | Process for preparing cycloalkyl compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5721340A (en) | 1982-02-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6113449B2 (de) | ||
| US4156093A (en) | Process for increasing the production or recovery yields of hemiacetal-esters of glyoxylic acid | |
| CN100364950C (zh) | 2-(烷基)环烯酮的制备方法 | |
| SU421177A3 (ru) | Способ получения низших алкиловых эфиров (±) дяс-хризантемовой кислоты | |
| JPH0129783B2 (de) | ||
| JPH0129782B2 (de) | ||
| EP0037588B1 (de) | Verfahren zur Herstellung von Furfurylalkoholen | |
| US4237322A (en) | Process for preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol | |
| HU208108B (en) | Process for producing alkoxy alkilidenemalonic acid esters | |
| EP0239992B1 (de) | Verfahren zur Herstellung von 2,3,4,5-Tetrafluorbenzoylacetaten | |
| JP3386596B2 (ja) | ５（ｅ），８（ｚ），１１（ｚ）−テトラデカトリエン−２−オンの製造方法 | |
| USRE31260E (en) | Process for the preparation of an acetonitrile derivative | |
| US3287372A (en) | Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones | |
| US2768967A (en) | Process for manufacture of 2, 5 diketo-8-nonen-3-ol | |
| US3468927A (en) | Process for preparing pimelic acid and a 2,2-dialkyl-1,3-propanediol | |
| US2857422A (en) | Production of carbonyl-substituted ethanol esters | |
| US5248798A (en) | Method of preparation of 8-hydroxyoctanoic acid | |
| SU1451139A1 (ru) | Способ получени коричного альдегида | |
| US4155929A (en) | Process for the preparation of an acetonitrile derivative | |
| JP2682687B2 (ja) | 新規チオフエン化合物およびそれらの製造 | |
| JPS6364416B2 (de) | ||
| JP3254746B2 (ja) | 末端アセチレン化合物およびその製造法 | |
| JP3838682B2 (ja) | ２−メチル−４−オキソ−２−シクロヘキセンカルボン酸エステル及びその新規中間体の製法 | |
| JP2759348B2 (ja) | ２―アルキル―３―アルコキシカルボニルメチルシクロペンタノンの製造法 | |
| JP2631769B2 (ja) | アリルイソアミルグリコレートの製造方法 |