JPS5929058B2 - 菊酸エステルの新規な製造法 - Google Patents
菊酸エステルの新規な製造法Info
- Publication number
- JPS5929058B2 JPS5929058B2 JP3830476A JP3830476A JPS5929058B2 JP S5929058 B2 JPS5929058 B2 JP S5929058B2 JP 3830476 A JP3830476 A JP 3830476A JP 3830476 A JP3830476 A JP 3830476A JP S5929058 B2 JPS5929058 B2 JP S5929058B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triphenylisopropylphosphonium
- butenoate
- oxo
- halide
- 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
- 239000002253 acid Substances 0.000 title claims description 12
- 150000002148 esters Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 235000007516 Chrysanthemum Nutrition 0.000 title claims description 7
- 244000189548 Chrysanthemum x morifolium Species 0.000 title claims 2
- -1 alkyl 4-oxo-2E-butenoate Chemical compound 0.000 claims description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- CRBJVPSOOMDSPT-NSCUHMNNSA-N methyl (e)-4-oxobut-2-enoate Chemical group COC(=O)\C=C\C=O CRBJVPSOOMDSPT-NSCUHMNNSA-N 0.000 claims description 4
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical group [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000723353 Chrysanthemum Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical class CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- VXJPCEOTZNHHOA-UHFFFAOYSA-N [K].OC Chemical compound [K].OC VXJPCEOTZNHHOA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- VFXPJEJTBCCTIQ-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 VFXPJEJTBCCTIQ-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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 |
|---|---|---|---|
| BE155169A BE827652A (fr) | 1975-04-07 | 1975-04-07 | Nouveau procede de preparation d'esters d'alcoyle inferieur de l'aldehyde hemicaronique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51127049A JPS51127049A (en) | 1976-11-05 |
| JPS5929058B2 true JPS5929058B2 (ja) | 1984-07-18 |
Family
ID=3842757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3830476A Expired JPS5929058B2 (ja) | 1975-04-07 | 1976-04-07 | 菊酸エステルの新規な製造法 |
| JP3830576A Pending JPS51127050A (en) | 1975-04-07 | 1976-04-07 | New process for manufacture of hemicaronic acid aldehyde lower alkyl ester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3830576A Pending JPS51127050A (en) | 1975-04-07 | 1976-04-07 | New process for manufacture of hemicaronic acid aldehyde lower alkyl ester |
Country Status (11)
| Country | Link |
|---|---|
| JP (2) | JPS5929058B2 (enExample) |
| BE (1) | BE827652A (enExample) |
| CA (1) | CA1091250A (enExample) |
| CH (1) | CH609027A5 (enExample) |
| DE (1) | DE2615160A1 (enExample) |
| DK (1) | DK134176A (enExample) |
| FR (1) | FR2306970A1 (enExample) |
| GB (1) | GB1502527A (enExample) |
| IE (1) | IE43363B1 (enExample) |
| IT (1) | IT1065993B (enExample) |
| NL (1) | NL7603678A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE827652A (fr) * | 1975-04-07 | 1975-10-07 | Nouveau procede de preparation d'esters d'alcoyle inferieur de l'aldehyde hemicaronique | |
| DE2923774A1 (de) * | 1979-06-12 | 1980-12-18 | Bayer Ag | Verfahren zur herstellung von 3,3-dimethyl-cyclopropan-1,2-dicarbonsaeureestern |
| DE2927133A1 (de) * | 1979-07-05 | 1981-01-08 | Bayer Ag | Verfahren zur herstellung von 2-formyl-3,3-dimethyl-cyclopropan1-carbonsaeureestern |
| FR2490633A1 (fr) * | 1980-09-24 | 1982-03-26 | Roussel Uclaf | Procede de preparation de derives d'acides cyclopropane carboxyliques porteurs d'une fonction aldehyde |
| FR2624511B1 (fr) * | 1987-12-11 | 1990-09-21 | Roussel Uclaf | Procede enantioselectif pour preparer des derives de l'aldehyde hemicaronique de structure trans ou cis |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE827652A (fr) * | 1975-04-07 | 1975-10-07 | Nouveau procede de preparation d'esters d'alcoyle inferieur de l'aldehyde hemicaronique |
-
1975
- 1975-04-07 BE BE155169A patent/BE827652A/xx not_active IP Right Cessation
-
1976
- 1976-03-26 DK DK134176A patent/DK134176A/da not_active IP Right Cessation
- 1976-03-31 FR FR7609336A patent/FR2306970A1/fr active Granted
- 1976-04-05 CA CA249,575A patent/CA1091250A/fr not_active Expired
- 1976-04-06 IE IE71976A patent/IE43363B1/en unknown
- 1976-04-06 GB GB1394176A patent/GB1502527A/en not_active Expired
- 1976-04-06 IT IT4888476A patent/IT1065993B/it active
- 1976-04-07 JP JP3830476A patent/JPS5929058B2/ja not_active Expired
- 1976-04-07 CH CH438276A patent/CH609027A5/xx not_active IP Right Cessation
- 1976-04-07 JP JP3830576A patent/JPS51127050A/ja active Pending
- 1976-04-07 NL NL7603678A patent/NL7603678A/xx not_active Application Discontinuation
- 1976-04-07 DE DE19762615160 patent/DE2615160A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1502527A (en) | 1978-03-01 |
| JPS51127050A (en) | 1976-11-05 |
| DE2615160A1 (de) | 1976-10-21 |
| IE43363B1 (en) | 1981-02-11 |
| JPS51127049A (en) | 1976-11-05 |
| FR2306970A1 (fr) | 1976-11-05 |
| DK134176A (da) | 1976-10-08 |
| IT1065993B (it) | 1985-03-04 |
| CA1091250A (fr) | 1980-12-09 |
| CH609027A5 (en) | 1979-02-15 |
| BE827652A (fr) | 1975-10-07 |
| IE43363L (en) | 1976-10-07 |
| NL7603678A (nl) | 1976-10-11 |
| FR2306970B1 (enExample) | 1979-10-05 |
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