GB1250869A - - Google Patents
Info
- Publication number
- GB1250869A GB1250869A GB1250869DA GB1250869A GB 1250869 A GB1250869 A GB 1250869A GB 1250869D A GB1250869D A GB 1250869DA GB 1250869 A GB1250869 A GB 1250869A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohex
- trimethyl
- hydroxy
- triphenyl
- penta
- 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
- -1 polyene compounds Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 abstract 3
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 abstract 3
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 abstract 2
- RANZORNCENEFNN-UHFFFAOYSA-M [3-methyl-5-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)penta-2,4-dienyl]-triphenylphosphanium bromide Chemical compound [Br-].O=C1C(=C(C(CC1)(C)C)C=CC(=CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C RANZORNCENEFNN-UHFFFAOYSA-M 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000004714 phosphonium salts Chemical class 0.000 abstract 2
- JUFKQNCQDFHWFD-UHFFFAOYSA-N (3S,7E,9R)-3,9-dihydroxy-5,7-megastigmadiene Natural products CC(O)C=CC1=C(C)CC(O)CC1(C)C JUFKQNCQDFHWFD-UHFFFAOYSA-N 0.000 abstract 1
- PPEXHEZQKRHDII-UHFFFAOYSA-N 3-(3-hydroxy-3-methylpenta-1,4-dienyl)-2,4,4-trimethylcyclohex-2-en-1-ol Chemical compound CC1=C(C=CC(C)(O)C=C)C(C)(C)CCC1O PPEXHEZQKRHDII-UHFFFAOYSA-N 0.000 abstract 1
- JUFKQNCQDFHWFD-MNOVXSKESA-N 3-Hydroxy-beta-ionol Natural products C[C@@H](O)C=CC1=C(C)C[C@H](O)CC1(C)C JUFKQNCQDFHWFD-MNOVXSKESA-N 0.000 abstract 1
- HFRZSVYKDDZRQY-AATRIKPKSA-N 3-Hydroxy-beta-ionone Chemical compound CC(=O)\C=C\C1=C(C)CC(O)CC1(C)C HFRZSVYKDDZRQY-AATRIKPKSA-N 0.000 abstract 1
- LICNQDPDQQOXCU-FYJFLYSWSA-N 3-Hydroxy-beta-ionone Natural products CC(=O)\C=C\C1=C(C)[C@@H](O)CCC1(C)C LICNQDPDQQOXCU-FYJFLYSWSA-N 0.000 abstract 1
- HXQRIVAUIRBXMR-UHFFFAOYSA-N 4-(3-hydroxy-3-methylpenta-1,4-dienyl)-3,5,5-trimethylcyclohex-3-en-1-ol Chemical compound CC1=C(C=CC(C)(O)C=C)C(C)(C)CC(O)C1 HXQRIVAUIRBXMR-UHFFFAOYSA-N 0.000 abstract 1
- JUFKQNCQDFHWFD-AATRIKPKSA-N 4-[(e)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-3-en-1-ol Chemical compound CC(O)\C=C\C1=C(C)CC(O)CC1(C)C JUFKQNCQDFHWFD-AATRIKPKSA-N 0.000 abstract 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- CMSYAQMBQAWCLD-UHFFFAOYSA-N [2,4,4-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-en-1-yl] acetate Chemical compound CC(=O)OC1CCC(C)(C)C(C=CC(C)=O)=C1C CMSYAQMBQAWCLD-UHFFFAOYSA-N 0.000 abstract 1
- TXHARUYWUGDGQT-UHFFFAOYSA-N [4-(3-acetyloxybut-1-ynyl)-3,5,5-trimethylcyclohex-3-en-1-yl] acetate Chemical compound CC(=O)OC(C)C#CC1=C(C)CC(OC(C)=O)CC1(C)C TXHARUYWUGDGQT-UHFFFAOYSA-N 0.000 abstract 1
- JFNJSIKHHNVBEF-UHFFFAOYSA-M [Br-].OC1C(=C(C(CC1)(C)C)C=CC(=CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C Chemical compound [Br-].OC1C(=C(C(CC1)(C)C)C=CC(=CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C)C JFNJSIKHHNVBEF-UHFFFAOYSA-M 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930002839 ionone Natural products 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- HFRZSVYKDDZRQY-UHFFFAOYSA-N rac-3-Hydroxy-beta-ionone Natural products CC(=O)C=CC1=C(C)CC(O)CC1(C)C HFRZSVYKDDZRQY-UHFFFAOYSA-N 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/10—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by etherified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,250,869. Manufacture of polyene compounds. F. HOFFMANN-LA ROCHE & CO. A.G. 16 July, 1970 [1 Aug., 1969], No. 34485/70. Headings C2C and C2P. The invention relates to a process for the manufacture of polyene compounds of a general formula in which the R-symbols have the same significance and each represents the 2-[4-hydroxy- 2,6,6 - trimethylcyclohex - 1 - en - 1 - yl]- vinyl, the 2 - [3 - hydroxy - 2,6,6 - trimethylcyclohex - 1 - en - 1 - yl] - vinyl or the 2- [3 - oxo - 2,6,6 - trimethyl - cyclohex - 1 - en- 1 - yl] - vinyl residue, which process comprises reacting the dialdehyde of the formula with a phosphonium salt of the general formula in which Y is an alkyl or di-(lower alkyl) amine group and Z is a halogen or hydrosulphate ion, in the presence of an ethylene oxide which may be substituted by C 1 -C 4 alkyl. Examples are described in which 2,7-dimethylocta-2,4-6-trien- 1, 8-dial is reacted with (a) [5-(4-hydroxy-2,6,6- trimethyl - cyclohex - 1 - en - 1 - yl) - 3 - methylenta - 2,4 - dienyl] - triphenyl - phosphonium bromide; (b) [5 - (3 - hydroxy - 2,6,6 - trimethyl - cyclohex - 1 - en - 1 - yl) - 3 - methylpenta 2,4 - dienyl] - triphenyl - phosphonium bromide; and (c) [5 - (3 - oxo - 2,6,6 - trimethylcyclohex - 1 - en - 1 - yl) - 3 - methyl - penta- 2,4 - dienyl] - triphenyl - phosphonium bromide. These phosphonium salts of Formula II are prepared respectively by (a) 4-(4-acetoxy-2,6,6- trimethyl - cyclohex - 1 - en - 1 - yl) - 2 - acetoxybut - 3 - yne is reduced to 3 - hydroxy - betaionol with the aid of a mixed metal hydride, which is then oxidized and the 3-hydroxy-betaionone thus obtained is then reacted with vinyl magnesium bromide to produce 5-(4-hydroxy- 2,6,6 - trimethyl - cyclohex - 1 - en - 1 - yl) - 3- methyl - penta - 1,4 - dien - 3 - ol which is reacted with triphenyl-phosphonium bromide; (b) Beta-ionone is reacted with ethyl orthoformate and the resulting ionone enol-ether is treated with a brominating agent and the 4- bromo-beta-ionone thus obtained is subsequently acylated and the resulting 4-(3- acetoxy - 2,6,6 - trimethyl - cyclohex - 1 - en- 1 - yl) - but - 3 - en - 2 - one - [4 - acetoxy - beta - ionone] is reactedwithvinyl-magnesium bromide, hydrolised and converted into [5-hydroxy-2,6,6- trimethyl - cyclohex - 1 - en - 1 - yl) - 3 - methyl penta - 2,4 - dienyl] - triphenyl - phosphonium bromide by treatment with triphenyl-phosphonium bromide; and (c) the 5-(3-hydroxy- 2,6,6 - trimethyl - cyclohex - 1 - en - 1 - yl)- 3 - methyl - penta - 1,4 - dien - 3 - ol is oxidized and the resulting 5 - (3 - oxo - 2,6,6 - trimethyl. cyclohex - 1 - en - 1 - yl) - 3 - methyl - penta- 1,4 - dien - 3 - ol is subsequently converted into [5 - (3 - oxo - 2,6,6 - trimethyl - cyclohex- 1 - en - 1 - yl) - 3 - methyl - penta - 2,4 - dienyl]- triphenyl - phosphonium bromide by treatment with triphenyl-phosphonium bromide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1172669A CH517053A (en) | 1969-08-01 | 1969-08-01 | Process for the preparation of polyene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1250869A true GB1250869A (en) | 1971-10-20 |
Family
ID=4376304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1250869D Expired GB1250869A (en) | 1969-08-01 | 1970-07-16 |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE754225A (en) |
| CH (1) | CH517053A (en) |
| DE (1) | DE2037935A1 (en) |
| FR (1) | FR2059582B1 (en) |
| GB (1) | GB1250869A (en) |
| NL (1) | NL7010549A (en) |
| SE (1) | SE366738B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653838A1 (en) * | 1975-11-30 | 1977-06-02 | Hoffmann La Roche | POLYENE COMPOUNDS |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000198A (en) * | 1975-06-09 | 1976-12-28 | Hoffmann-La Roche Inc. | Hydroxy-acetylene-substituted cyclohexenone |
| US4098827A (en) * | 1977-01-17 | 1978-07-04 | Hoffmann-La Roche Inc. | 1-(2,6,6-Trimethyl-3-hydroxy-1-cyclohexen-1-yl)-3-methyl-penta-1,4-diene[or 1-yn-4-EN]-3-ols |
| USRE30260E (en) | 1977-01-17 | 1980-04-22 | Hoffmann-La Roche Inc. | 1-(2,6,6-Trimethyl-3-hydroxy-1-cyclohexen-1-yl)-3-methyl-penta-1,4-diene[or 1-yn-4-en]-3-ols |
| DK171297B1 (en) * | 1987-03-27 | 1996-08-26 | Hoffmann La Roche | Process for the preparation of cyclohexene derivatives as intermediates for the preparation of zeaxanthin and cyclohexene derivatives |
-
0
- BE BE754225D patent/BE754225A/en unknown
-
1969
- 1969-08-01 CH CH1172669A patent/CH517053A/en not_active IP Right Cessation
-
1970
- 1970-07-16 NL NL7010549A patent/NL7010549A/xx unknown
- 1970-07-16 GB GB1250869D patent/GB1250869A/en not_active Expired
- 1970-07-21 FR FR707026764A patent/FR2059582B1/fr not_active Expired
- 1970-07-28 SE SE10381/70A patent/SE366738B/xx unknown
- 1970-07-30 DE DE19702037935 patent/DE2037935A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653838A1 (en) * | 1975-11-30 | 1977-06-02 | Hoffmann La Roche | POLYENE COMPOUNDS |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2059582B1 (en) | 1973-01-12 |
| BE754225A (en) | 1971-02-01 |
| FR2059582A1 (en) | 1971-06-04 |
| CH517053A (en) | 1971-12-31 |
| NL7010549A (en) | 1971-02-03 |
| DE2037935A1 (en) | 1971-02-11 |
| SE366738B (en) | 1974-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |