IL32433A - Octahydro-1,2,4-methenopentalene-5-carboxylic acid alkoxyalkyl esters and process for their production - Google Patents
Octahydro-1,2,4-methenopentalene-5-carboxylic acid alkoxyalkyl esters and process for their productionInfo
- Publication number
- IL32433A IL32433A IL32433A IL3243369A IL32433A IL 32433 A IL32433 A IL 32433A IL 32433 A IL32433 A IL 32433A IL 3243369 A IL3243369 A IL 3243369A IL 32433 A IL32433 A IL 32433A
- Authority
- IL
- Israel
- Prior art keywords
- octahydro
- carboxylic acid
- methenopentalene
- ester
- nickel
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 12
- -1 acrylic acid alkoxyalkyl ester Chemical class 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 5
- BTBORDOYETVCHQ-UHFFFAOYSA-N C(=O)=C1C(C(C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)=C=O)=C=O.[Ni] Chemical compound C(=O)=C1C(C(C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)=C=O)=C=O.[Ni] BTBORDOYETVCHQ-UHFFFAOYSA-N 0.000 claims description 4
- XUAXJVSYRMEROP-UHFFFAOYSA-N C1C2=CC=3C(C(=CC13)C(=O)O)=C2 Chemical compound C1C2=CC=3C(C(=CC13)C(=O)O)=C2 XUAXJVSYRMEROP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 2
- LXAOOPAIGYABHJ-UHFFFAOYSA-N CCOCCOC(C1=CC(C2)=C3C1=CC2=C3)=O Chemical compound CCOCCOC(C1=CC(C2)=C3C1=CC2=C3)=O LXAOOPAIGYABHJ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 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 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- VOKXPKSMYJLAIW-UHFFFAOYSA-N nickel;phosphane Chemical class P.[Ni] VOKXPKSMYJLAIW-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- BRLPPEPJJLDMAD-UHFFFAOYSA-N octahydro-1,2,4-methenopentalene Chemical compound C1C2C3CCC2C2C3C21 BRLPPEPJJLDMAD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- AGHFSJKIWBGYTC-UHFFFAOYSA-N pentalene-2-carboxylic acid Chemical compound C1=CC2=CC(C(=O)O)=CC2=C1 AGHFSJKIWBGYTC-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- COKUUKLSHSDZMZ-UHFFFAOYSA-N tricyclo[4.2.1.03,7]nona-1,3,5,7-tetraene Chemical compound C12=CC=C3C=C(C=C13)C2 COKUUKLSHSDZMZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH921268A CH498799A (de) | 1968-06-20 | 1968-06-20 | Verfahren zur Herstellung von Octahydro-1,2,4-methenopentalen-5-carbonsäure-nieder-alkoxyalkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32433A0 IL32433A0 (en) | 1969-08-27 |
| IL32433A true IL32433A (en) | 1972-05-30 |
Family
ID=4349571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32433A IL32433A (en) | 1968-06-20 | 1969-06-19 | Octahydro-1,2,4-methenopentalene-5-carboxylic acid alkoxyalkyl esters and process for their production |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT291218B (cs) |
| BE (1) | BE734865A (cs) |
| BR (1) | BR6909942D0 (cs) |
| CH (1) | CH498799A (cs) |
| CS (1) | CS154275B2 (cs) |
| DE (1) | DE1931152A1 (cs) |
| ES (1) | ES368536A1 (cs) |
| FR (1) | FR2011308A1 (cs) |
| GB (1) | GB1206099A (cs) |
| IL (1) | IL32433A (cs) |
| NL (1) | NL6909401A (cs) |
| RO (1) | RO56638A (cs) |
| SE (1) | SE357733B (cs) |
-
1968
- 1968-06-20 CH CH921268A patent/CH498799A/de not_active IP Right Cessation
-
1969
- 1969-06-16 SE SE08528/69A patent/SE357733B/xx unknown
- 1969-06-19 AT AT584969A patent/AT291218B/de not_active IP Right Cessation
- 1969-06-19 BE BE734865D patent/BE734865A/xx unknown
- 1969-06-19 DE DE19691931152 patent/DE1931152A1/de active Pending
- 1969-06-19 NL NL6909401A patent/NL6909401A/xx unknown
- 1969-06-19 RO RO60283A patent/RO56638A/ro unknown
- 1969-06-19 FR FR6920543A patent/FR2011308A1/fr not_active Withdrawn
- 1969-06-19 IL IL32433A patent/IL32433A/en unknown
- 1969-06-19 CS CS434369A patent/CS154275B2/cs unknown
- 1969-06-19 BR BR209942/69A patent/BR6909942D0/pt unknown
- 1969-06-19 ES ES368536A patent/ES368536A1/es not_active Expired
- 1969-06-19 GB GB31156/69A patent/GB1206099A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2011308A1 (cs) | 1970-02-27 |
| AT291218B (de) | 1971-07-12 |
| CH498799A (de) | 1970-11-15 |
| NL6909401A (cs) | 1969-12-23 |
| CS154275B2 (cs) | 1974-03-29 |
| BR6909942D0 (pt) | 1973-02-08 |
| BE734865A (cs) | 1969-12-19 |
| ES368536A1 (es) | 1971-05-01 |
| GB1206099A (en) | 1970-09-23 |
| RO56638A (cs) | 1974-08-01 |
| DE1931152A1 (de) | 1970-01-02 |
| SE357733B (cs) | 1973-07-09 |
| IL32433A0 (en) | 1969-08-27 |
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