GB1079217A - Method of increasing the chain length of aldehydes - Google Patents

Method of increasing the chain length of aldehydes

Info

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
Application number
GB48228/64A
Inventor
Herwig Freyschlag
Werner Reif
Axel Nuerrenbach
Herst Pommer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1079217A publication Critical patent/GB1079217A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00Derivatives 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
    • C07C403/14Derivatives 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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
    • C07C45/72Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/535Organo-phosphoranes
    • C07F9/5352Phosphoranes containing the structure P=C-
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems 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.
GB48228/64A 1963-11-30 1964-11-27 Method of increasing the chain length of aldehydes Expired GB1079217A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (11)

* Cited by examiner, † Cited by third party
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
DE1210780C2 (en) 1966-08-25
AT249279B (en) 1966-09-12
ES306554A1 (en) 1965-04-01
DE1210780B (en) 1966-02-17
BR6464831D0 (en) 1973-08-09
NL6413904A (en) 1965-05-31
FR1453252A (en) 1966-06-03
BE656435A (en) 1965-05-31
CH440243A (en) 1967-07-31
NL124613C (en)

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