GB1351919A - Process for the preparation of methyl jasmonate - Google Patents
Process for the preparation of methyl jasmonateInfo
- Publication number
- GB1351919A GB1351919A GB5672172A GB5672172A GB1351919A GB 1351919 A GB1351919 A GB 1351919A GB 5672172 A GB5672172 A GB 5672172A GB 5672172 A GB5672172 A GB 5672172A GB 1351919 A GB1351919 A GB 1351919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- prepared
- treating
- methyl jasmonate
- 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
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 title abstract 3
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 2
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- 229930188970 Justin Natural products 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- ZNJFBWYDHIGLCU-UHFFFAOYSA-N jasmonic acid Natural products CCC=CCC1C(CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-UHFFFAOYSA-N 0.000 abstract 1
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D317/72—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 spiro-condensed with carbocyclic rings
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1351919 Methyl jasmonate SOC ANON DES ETABS ROURE-BERTRAND FILS & JUSTIN DUPONT 8 Dec 1972 [10 Dec 1971] 56721/72 Heading C2C Methyl jasmonate having the Formula I is prepared by treating a dialkyl malonate derivative of the Formula II where R is an alkyl group having 1 to 4 carbon atoms, with water under pressure and at elevated temperature, and methylating the resulting jasmonic acid. The compound of Formula II may be prepared by the addition of a malonate of the Formula III, to a compound of the Formula IV Compound IV is prepared by treating a compound of Formula XI with sulphuryl chloride; compound XI is prepared by hydrogenating a compound of Formula IX and treating the hydrogenated product with ptoluene-sulphonic acid; compound IX is prepared by refluxing a compound of Formula VIII with a suspension of sodium amide in anhydrous isopropyl ether and thereafter adding diethyl sulphate; compound VIII is prepared by heating together ethylene glycol, p-toluene sulphonic acid and a compound of Formula VII compound VII is prepared by reacting pyrrolidine and p-toluenesulphonic acid with cyclopentanone and hydrolysing.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7144417A FR2164034A5 (en) | 1971-12-10 | 1971-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1351919A true GB1351919A (en) | 1974-05-15 |
Family
ID=9087271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5672172A Expired GB1351919A (en) | 1971-12-10 | 1972-12-08 | Process for the preparation of methyl jasmonate |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE791801A (en) |
| BR (1) | BR7208571D0 (en) |
| CA (1) | CA978203A (en) |
| CH (1) | CH570967A5 (en) |
| ES (1) | ES409446A1 (en) |
| FR (1) | FR2164034A5 (en) |
| GB (1) | GB1351919A (en) |
| IT (1) | IT983176B (en) |
| NL (1) | NL7216712A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349640A (en) * | 2021-12-17 | 2022-04-15 | 山东新和成药业有限公司 | Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method |
-
0
- BE BE791801D patent/BE791801A/en unknown
-
1971
- 1971-12-10 FR FR7144417A patent/FR2164034A5/fr not_active Expired
-
1972
- 1972-11-21 CA CA157,068A patent/CA978203A/en not_active Expired
- 1972-11-30 CH CH1743472A patent/CH570967A5/xx not_active IP Right Cessation
- 1972-11-30 IT IT3235672A patent/IT983176B/en active
- 1972-12-06 BR BR857172A patent/BR7208571D0/en unknown
- 1972-12-08 GB GB5672172A patent/GB1351919A/en not_active Expired
- 1972-12-08 NL NL7216712A patent/NL7216712A/xx unknown
- 1972-12-09 ES ES409446A patent/ES409446A1/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349640A (en) * | 2021-12-17 | 2022-04-15 | 山东新和成药业有限公司 | Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method |
| CN114349640B (en) * | 2021-12-17 | 2024-03-22 | 山东新和成药业有限公司 | Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2260447A1 (en) | 1973-06-14 |
| BR7208571D0 (en) | 1973-12-18 |
| CH570967A5 (en) | 1975-12-31 |
| FR2164034A5 (en) | 1973-07-27 |
| BE791801A (en) | 1973-05-23 |
| ES409446A1 (en) | 1976-04-16 |
| CA978203A (en) | 1975-11-18 |
| IT983176B (en) | 1974-10-31 |
| DE2260447B2 (en) | 1976-05-20 |
| NL7216712A (en) | 1973-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |