GB751573A - A polyene dialdehyde and process for the manufacture thereof - Google Patents

A polyene dialdehyde and process for the manufacture thereof

Info

Publication number
GB751573A
GB751573A GB23436/54A GB2343654A GB751573A GB 751573 A GB751573 A GB 751573A GB 23436/54 A GB23436/54 A GB 23436/54A GB 2343654 A GB2343654 A GB 2343654A GB 751573 A GB751573 A GB 751573A
Authority
GB
United Kingdom
Prior art keywords
ine
dial
dimethyl
acid
tetramethyl
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
GB23436/54A
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB751573A publication Critical patent/GB751573A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having 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
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 2,6,11,15-tetramethyl - hexadecahexen - (2,4,6,10,12,14) - ine-(8) - dial - (1,16) and a process for its preparation by acetalizing 4,9-dimethyl-dodecatetraen-(2,4,8,10) - ine - (6) - dial - (1,12), condensing the diacetal so obtained with a propenyl ether in the presence of an acidic condensing agent and treating the resulting 3,14-dietherified 2,6,11,15 - tetramethyl - hexadecatetraen-(4,6,10,12) - ine - (8) - diacetal - (1,16) with an acid agent to effect hydrolysis of the acetal groups and elimination of alcohol from between positions 2 and 3, and 14 and 15. Specified acid condensing agents are boron trifluoride-ether complex, zinc chloride, aluminium chloride, and the tetrachlorides of titanium and tin, whilst the acid agent used for the hydrolysis of the acetal groups is a water-soluble non-volatile organic or inorganic acid, e.g. p-toluene sulphonic, acetic, propionic, sulphuric or phosphoric acids, or a water-soluble salt having an acid reaction, e.g. zinc chloride or sodium hydrogen sulphate. In an example 4,9-dimethyl-dodecatetraen - (2,4,8,10) - ine - (6) - dial (1,12) in ethyl orthoformate is heated with ethanolic ammonium nitrate to yield the corresponding di(diethyl acetal)-(1,12), which is treated with ethyl propenyl ether and boron trifluoride-ether complex to produce 3,14-diethoxy-2,6,11, 15 - tetramethyl - hexadecatetraen - (4,6,10,12)-ine - (8) - di(diethyl acetal) - (1,16). Hydrolysis with phosphoric acid in aqueous dioxan containing a trace of hydroquinone yields 2,6,11,15 - tetramethyl - hexadecahexen-(2,4,6,10,12,14)-ine-(8)-dial-(1,16). The Specification also refers to the formation of dehydro-methyl bixin, dehydro-crocetin and dehydro-bixin dialdehyde from the novel compound of the invention. 4,9 - Dimethyl - dodecatetraen - (2,4,8,10) - ine-(6) - dial - (1,12) is prepared by acetalizing 2,7 - dimethyl - octadien - (2,6) - ine - (4) - dial-(1,8) with ethyl-ortho-formate in the presence of ammonium nitrate, condensing the product with ethyl vinyl ether and hydrolysing the 3,10-dietherified - 4,9 - dimethyl - dodecadien - (4,8)-ine - (6) - diacetal - (1,12) with aqueous phosphoric acid.
GB23436/54A 1953-08-14 1954-08-12 A polyene dialdehyde and process for the manufacture thereof Expired GB751573A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH751573X 1953-08-14

Publications (1)

Publication Number Publication Date
GB751573A true GB751573A (en) 1956-06-27

Family

ID=4533929

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23436/54A Expired GB751573A (en) 1953-08-14 1954-08-12 A polyene dialdehyde and process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB751573A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3103352A1 (en) 2015-06-12 2016-12-14 DSM IP Assets B.V. Acid stable beverages comprising bixin
WO2016198570A1 (en) 2015-06-12 2016-12-15 Dsm Ip Assets B.V. New natural color for edible coatings
WO2016198569A1 (en) 2015-06-12 2016-12-15 Dsm Ip Assets B.V. New orange color for edible coatings

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3103352A1 (en) 2015-06-12 2016-12-14 DSM IP Assets B.V. Acid stable beverages comprising bixin
WO2016198567A1 (en) 2015-06-12 2016-12-15 Dsm Ip Assets B.V. Acid stable beverages comprising bixin
WO2016198570A1 (en) 2015-06-12 2016-12-15 Dsm Ip Assets B.V. New natural color for edible coatings
WO2016198569A1 (en) 2015-06-12 2016-12-15 Dsm Ip Assets B.V. New orange color for edible coatings

Similar Documents

Publication Publication Date Title
DE3361231D1 (en) Process for the preparation of alkyl glucosides
GB1435887A (en) Oxygenated alicyclic derivatives useful as odoriferous and flavouring ingredients
GB1379870A (en) Process for the production of quinoxaline
GB751573A (en) A polyene dialdehyde and process for the manufacture thereof
GB1514076A (en) Carotenoid and process for the manufacture thereof
GB935006A (en) Improvements in or relating to isoprene derivatives of trimethyl cyclohexene
GB821388A (en) Method of preparing alkali metal hypophosphites
GB1039376A (en) Process for preparing bis-hydroxyalkylsulphones and ª‰-hydroxyalkylsulphonic acid salts
GB1176248A (en) Novel 13-Alkyl-Des-A-10-Aza-Gonenes and Processes for Preparing Hexahydroindanes therefrom
ATE9229T1 (en) PROCESS FOR THE PREPARATION OF A CEPHEMCARBONATE DERIVATIVE.
GB1309332A (en) Substituted pentenes
GB737606A (en) Preparation of aldehydopentadecanoic acid and dialdehydotetradecane
GB1312193A (en) Process for the manufacture of 6,6-alkylenedioxyheptan-2-ones
GB774563A (en) Process for the production of hydroxyalkane-sulphonic acids from their salts
GB788303A (en) A novel acetoacetate and a process for the manufacture thereof
ES447636A1 (en) Process for manufacture of 3,5-ditert.butyl-4-hydroxybenzaldehyde from 3,5-ditert.butyl-4-hydroxybenzyl alcohol
GB547027A (en) Improvements in or relating to the manufacture of bis-oxyphenyl compounds
GB969815A (en) Process for the production of trans-dec-2-en-9-one-1-acid
GB788302A (en) The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom
GB816210A (en) Trimethylolpropane
GB630865A (en) Improvements in or relating to the production of compounds having vitamin a activity and the intermediates thereof
GB1164330A (en) Process for manufacturing Pyridoxal-5-Phosphate
GB886577A (en) A process for the manufacture of unsaturated alcohols and acyl derivatives thereof
GB769192A (en) Process for the manufacture of hydroxyphenyl-serines
GB610859A (en) A process for the manufacture of an antibacterial substance