GB1079217A - Method of increasing the chain length of aldehydes - Google Patents
Method of increasing the chain length of aldehydesInfo
- Publication number
- GB1079217A GB1079217A GB48228/64A GB4822864A GB1079217A GB 1079217 A GB1079217 A GB 1079217A GB 48228/64 A GB48228/64 A GB 48228/64A GB 4822864 A GB4822864 A GB 4822864A GB 1079217 A GB1079217 A GB 1079217A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carotinal
- apo
- reacted
- methylene
- give
- 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
- 150000001299 aldehydes Chemical class 0.000 title abstract 7
- 239000011604 retinal Substances 0.000 abstract 4
- -1 aralkyl radical Chemical class 0.000 abstract 3
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 235000020945 retinal Nutrition 0.000 abstract 2
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 abstract 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 abstract 1
- FYMHMXSHJBVJKH-UHFFFAOYSA-N CC(=C)C=CC=C(C=CC=C(C=O)C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC(=C)C=CC=C(C=CC=C(C=O)C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 FYMHMXSHJBVJKH-UHFFFAOYSA-N 0.000 abstract 1
- MRNLTGASYXDLCG-UHFFFAOYSA-N CC(=C)C=CC=C(C=O)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC(=C)C=CC=C(C=O)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 MRNLTGASYXDLCG-UHFFFAOYSA-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000004417 unsaturated alkyl group Chemical group 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
- C07C403/14—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
-
- 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
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
-
- 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
Polyunsaturated aldehydes are produced by reacting an aldehyde with an ylenal of formula <FORM:1079217/C2/1> in which Ar is an aryl radical which may be substituted by alkyl or alkoxy groups; R1, R2 and R3 are hydrogen or alkyl groups, and n is an integer from 1 to 6. The reaction takes place according to the following equation <FORM:1079217/C2/2> <FORM:1079217/C2/3> in which R4 may be a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl radical. The radical R4 may contain, for example, the group <FORM:1079217/C2/4> Dialdehydes may also be used as starting materials and in that case two molecules of ylenal are reacted with one molecule of dialdehyde. Examples of suitable starting aldehydes are b -ionylidene acetaldehyde, b -retinene, a -retinene, b -apo-141-carotinal, b -apo-81-carotinal, b -apo-121-carotinal, b -apo-101-carotinal, b -apo-61-carotinal and the aldehydes OHC-C(CH3) = CH-CH = CH-CH = C(CH3)-CHO, OHC-CH = CH-C(CH3) = CH-CH = CH-CH = C(CH3)-CH = CH-CHO and OHC-C(CH3) = CH-CH = CH-C(CH3) = CH-CH = CH-CH = C(CH3)-CH = CH-CH-C(CH3) CHO. Suitable ylenals are for example those in which the aryl groups are all phenyl groups. The aldehydes obtained can be further reacted with an ylenal to get a longer-chained aldehyde. In the examples (a) Vitamin A aldehyde is reacted with triphenyl phosphine-2-formylpropen-1-yl-methylene to give b -apo-121-carotinal; (b) b -apo-121-carotinal is reacted with triphenylphosphine - 2 - formylpropen - 1 - yl-methylene to give b -apo-81-carotinal; (c) triphenyl formyl buten-2-yl-1-phosphonium chloride is reacted with triphenylphosphine-2-formylpropen-1-yl-methylene and the product is reacted with Vitamin A aldehyde to give b -apo-81-carotinal; and (d) triphenyl-3-formylbuten-2-yl-1-phosphonium chloride is reacted with triphenylphosphine - 2 - formylpropen - 1 - yl methylene to give triphenyl phosphine-2,6-dimethyl - 6 - formylhexatriene - 1,3,5 - yl-methylene which is reacted with triphenyl-3-formyl-butene-2-yl-1-phosphonium chloride to give triphenylphosphine - 2,6,10 - trimethyl-10 - formyl decapentaene - 1,3,5,7,9 - yl-methylene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB74476A DE1210780B (en) | 1963-11-30 | 1963-11-30 | Process for the production of polyunsaturated aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1079217A true GB1079217A (en) | 1967-08-16 |
Family
ID=6978274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48228/64A Expired GB1079217A (en) | 1963-11-30 | 1964-11-27 | Method of increasing the chain length of aldehydes |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT249279B (en) |
| BE (1) | BE656435A (en) |
| BR (1) | BR6464831D0 (en) |
| CH (1) | CH440243A (en) |
| DE (1) | DE1210780B (en) |
| ES (1) | ES306554A1 (en) |
| FR (1) | FR1453252A (en) |
| GB (1) | GB1079217A (en) |
| NL (2) | NL6413904A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201727A (en) | 1976-11-14 | 1980-05-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4266073A (en) * | 1975-11-14 | 1981-05-05 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4299995A (en) | 1979-05-10 | 1981-11-10 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
| US4321209A (en) | 1975-11-14 | 1982-03-23 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4335248A (en) | 1975-11-14 | 1982-06-15 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
| US4338253A (en) | 1975-11-14 | 1982-07-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4375563A (en) | 1975-11-14 | 1983-03-01 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4395575A (en) | 1975-11-14 | 1983-07-26 | Hoffmann-La Roche, Inc. | 5(Halophenyl)-2-fluoro-pentadienals |
| CN112782309A (en) * | 2020-12-29 | 2021-05-11 | 常州大学 | Method for stabilizing long-chain unsaturated olefine aldehyde |
| CN115490728A (en) * | 2022-10-17 | 2022-12-20 | 杭州师范大学 | Synthesis method of allyl phosphine derivative |
-
0
- NL NL124613D patent/NL124613C/xx active
-
1963
- 1963-11-30 DE DEB74476A patent/DE1210780B/en active Granted
-
1964
- 1964-11-17 AT AT971964A patent/AT249279B/en active
- 1964-11-26 BR BR164831/64A patent/BR6464831D0/en unknown
- 1964-11-26 CH CH1527364A patent/CH440243A/en unknown
- 1964-11-27 GB GB48228/64A patent/GB1079217A/en not_active Expired
- 1964-11-30 ES ES0306554A patent/ES306554A1/en not_active Expired
- 1964-11-30 NL NL6413904A patent/NL6413904A/xx unknown
- 1964-11-30 BE BE656435D patent/BE656435A/xx unknown
- 1964-11-30 FR FR996862A patent/FR1453252A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4266073A (en) * | 1975-11-14 | 1981-05-05 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4321209A (en) | 1975-11-14 | 1982-03-23 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4335248A (en) | 1975-11-14 | 1982-06-15 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
| US4338253A (en) | 1975-11-14 | 1982-07-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4375563A (en) | 1975-11-14 | 1983-03-01 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4395575A (en) | 1975-11-14 | 1983-07-26 | Hoffmann-La Roche, Inc. | 5(Halophenyl)-2-fluoro-pentadienals |
| US4201727A (en) | 1976-11-14 | 1980-05-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
| US4299995A (en) | 1979-05-10 | 1981-11-10 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
| CN112782309A (en) * | 2020-12-29 | 2021-05-11 | 常州大学 | Method for stabilizing long-chain unsaturated olefine aldehyde |
| CN115490728A (en) * | 2022-10-17 | 2022-12-20 | 杭州师范大学 | Synthesis method of allyl phosphine derivative |
| CN115490728B (en) * | 2022-10-17 | 2023-12-08 | 杭州师范大学 | Synthesis method of allyl phosphine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6464831D0 (en) | 1973-08-09 |
| BE656435A (en) | 1965-05-31 |
| FR1453252A (en) | 1966-06-03 |
| DE1210780C2 (en) | 1966-08-25 |
| ES306554A1 (en) | 1965-04-01 |
| NL6413904A (en) | 1965-05-31 |
| NL124613C (en) | |
| DE1210780B (en) | 1966-02-17 |
| AT249279B (en) | 1966-09-12 |
| CH440243A (en) | 1967-07-31 |
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