GB1153375A - Process for the Cyclization of Unsaturated Organic Compounds - Google Patents
Process for the Cyclization of Unsaturated Organic CompoundsInfo
- Publication number
- GB1153375A GB1153375A GB26230/67A GB2623067A GB1153375A GB 1153375 A GB1153375 A GB 1153375A GB 26230/67 A GB26230/67 A GB 26230/67A GB 2623067 A GB2623067 A GB 2623067A GB 1153375 A GB1153375 A GB 1153375A
- Authority
- GB
- United Kingdom
- Prior art keywords
- yields
- acid
- organic compounds
- unsaturated organic
- acetate
- 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
- 150000002894 organic compounds Chemical class 0.000 title abstract 3
- 238000007363 ring formation reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 abstract 1
- VBEHOHGWCPGXSO-UHFFFAOYSA-N (3-propan-2-ylidenecyclopentyl) acetate Chemical compound C(C)(=O)OC1CC(CC1)=C(C)C VBEHOHGWCPGXSO-UHFFFAOYSA-N 0.000 abstract 1
- SRBNSUPEEJZGCH-UHFFFAOYSA-N (4-acetyloxycyclohexyl) acetate Chemical compound CC(=O)OC1CCC(OC(C)=O)CC1 SRBNSUPEEJZGCH-UHFFFAOYSA-N 0.000 abstract 1
- YTBAVQWJHNZHPQ-UHFFFAOYSA-N 1-(2-cyclohex-2-en-1-ylethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCC2C=CCCC2)=C1 YTBAVQWJHNZHPQ-UHFFFAOYSA-N 0.000 abstract 1
- IWJFILFTASNSOL-UHFFFAOYSA-N 4-(2-cyclohex-2-en-1-ylethyl)-1,2-dimethoxybenzene Chemical compound COC=1C=C(C=CC1OC)CCC1C=CCCC1 IWJFILFTASNSOL-UHFFFAOYSA-N 0.000 abstract 1
- BMDFTBXRFIRKAJ-UHFFFAOYSA-N 6,7-dimethoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4-ol Chemical compound OC1CCCC2CCC3=CC(=C(C=C3C12)OC)OC BMDFTBXRFIRKAJ-UHFFFAOYSA-N 0.000 abstract 1
- KUFDSEQTHICIIF-UHFFFAOYSA-N 6-methylhepta-1,5-diene Chemical compound CC(C)=CCCC=C KUFDSEQTHICIIF-UHFFFAOYSA-N 0.000 abstract 1
- OSHFMXBERJCBLB-UHFFFAOYSA-N 7-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4-ol Chemical compound OC1CCCC2CCC3=CC(=CC=C3C12)OC OSHFMXBERJCBLB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- MQNAWGURFBPDMW-UHFFFAOYSA-N cyclohex-2-en-1-yl acetate Chemical compound CC(=O)OC1CCCC=C1 MQNAWGURFBPDMW-UHFFFAOYSA-N 0.000 abstract 1
- ABZZOPIABWYXSN-UHFFFAOYSA-N cyclohex-3-en-1-ol Chemical compound OC1CCC=CC1 ABZZOPIABWYXSN-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 abstract 1
- -1 monohydrogen phosphate anion Chemical class 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- RURREWSZSUQSNB-UHFFFAOYSA-N pent-4-enylbenzene Chemical compound C=CCCCC1=CC=CC=C1 RURREWSZSUQSNB-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/22—All rings being cycloaliphatic the ring system containing eight carbon atoms, e.g. pentalene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,153,375. Cyclization of unsaturated organic compounds. RHONE-POULENC S.A. 7 June, 1967 [8 June, 1966], No. 26230/67. Heading C2C. [Also in Division C5] Unsaturated organic compounds having two carbon-carbon double bonds in the 1,5- or 1,6- positions are cyclized by mixing them with a mercuric salt in a sufficient proportion to provide one mercury ion for each pair of double bonds, adding to the mixture a proton acid the anion of which is not more nucleophilic than the monohydrogen phosphate anion, or a Lewis acid, and heating the mixture. The mercuric salt may be mercuric acetate, and the reaction may be effected at 60-90‹ C., optionally in a medium comprising a lower alkanoic acid, e.g. acetic acid. In the examples, in each of which perchloric acid is used as the proton acid, (1) diallyl yields cyclohexen-3-yl acetate and cyclohexane-1,4-diol diacetate or (Example 2) 4- cyclohexenol; (3) 2 - methyl - 2,6 - heptadiene yields 3-isopropylidene-cyclopentyl acetate; (4) 5-phenyl-1-pentene yields a product of the formula which is hydrolysed to yield a product of the formula (5) 3 - [2 - (3,4 - dimethoxyphenyl)ethyl]- cyclohexene yields 4 - hydroxy - 6,7 - dimethoxy - 1,2,3,4,4a,9,10,10a - octahydrophenanthrene; (6) 3 - [2 - (3 - methoxyphenyl) - ethyl] - cyclohexene yields 4 - hydroxy - 7 - methoxy - 1,2,3,4,4a,9,10,10a - octahydrophenanthrene; (7) cyclooctadiene yields products of the formulµ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR64698A FR1490605A (en) | 1966-06-08 | 1966-06-08 | Process of cyclization of unsaturated organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1153375A true GB1153375A (en) | 1969-05-29 |
Family
ID=8610471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26230/67A Expired GB1153375A (en) | 1966-06-08 | 1967-06-07 | Process for the Cyclization of Unsaturated Organic Compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3562316A (en) |
| CH (1) | CH520086A (en) |
| DE (1) | DE1618831B1 (en) |
| FR (1) | FR1490605A (en) |
| GB (1) | GB1153375A (en) |
| NL (1) | NL6707851A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159989A (en) * | 1977-05-02 | 1979-07-03 | Standard Oil Company (Indiana) | Process for preparing ethylene glycol diacylate |
| DE3360520D1 (en) * | 1982-06-03 | 1985-09-12 | Givaudan & Cie Sa | Cyclohex(en)yl methanols and their esters, with perfuming properties |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE560018A (en) * | 1956-08-14 |
-
1966
- 1966-06-08 FR FR64698A patent/FR1490605A/en not_active Expired
-
1967
- 1967-06-05 US US643389A patent/US3562316A/en not_active Expired - Lifetime
- 1967-06-06 NL NL6707851A patent/NL6707851A/xx unknown
- 1967-06-07 GB GB26230/67A patent/GB1153375A/en not_active Expired
- 1967-06-08 DE DE1967R0046214 patent/DE1618831B1/en not_active Withdrawn
- 1967-06-08 CH CH809667A patent/CH520086A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH520086A (en) | 1972-03-15 |
| DE1618831B1 (en) | 1972-01-05 |
| NL6707851A (en) | 1967-12-11 |
| US3562316A (en) | 1971-02-09 |
| FR1490605A (en) | 1967-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |