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    Production of mono-and poly-unsaturated aldehydes or their functional derivatives
    94.
    发明专利
    Production of mono-and poly-unsaturated aldehydes or their functional derivatives 未知

    公开(公告)号：GB1078858A

    公开(公告)日：1967-08-09

    申请号：GB4822964

    申请日：1964-11-27

    Applicant: BASF AG

    Inventor： FREYSCHLAG HERWIG ,  REIF WERNER ,  NUERRENBACH AXEL ,  POMMER HORST

    IPC: C07F9/54

    Abstract: Mono- or poly-unsaturated aldehydes or their functional derivatives are prepared by reacting an acetal, hemiacetal, mercaptal, aminal, acylal, oxime, hydrazone, semicarbazone or Schiff's base derivative prepared from phosphonium salts having the formula in which Ar denotes an aryl radical optionally substituted by alkyl or alkoxy groups, X is an anion, and n is an integer from 0 to 6, with a proton acceptor to convert the compounds into their ylids which are simultaneously or subsequently reacted with aldehydes or ketones by a Wittig reaction. The aldehyde derivatives so obtained may be hydrolysed to the corresponding aldehydes. Examples of phosphonium salts of Formula III mentioned are triphenylformylmethyl phosphonium chloride, triphenyl-b -formylcrotyl phosphonium chloride, triphenyl-b -formylcrotyl phosphonium bromide, triphenyl-a - formylcrotyl phosphonium chloride, triphenyl - 5 - formyl - 5 - methylpentadiene - (2,4)-yl phosphonium chloride, and triphenyl-7-formyl - 3,7 - dimethylheptatriene(2,4,6)-yl phosphonium chloride. Suitable proton acceptors are, for example, sodium alcoholates, ammonia, amines and aqueous alkali solutions such as caustic soda or potash solution. Suitable aldehydes or ketones to be reacted with the ylids are, for example, b -ionone, a -ionone, C14- aldehyde, b -ionylidene acetaldehyde, retinene, the apocarotenals and carotene dialdehydes. Examples are given of the preparation of (a) the tetraethyl acetal of crocetin dialdehyde, (b) b -apo-121-carotenal; (c) b -apo-81-carotenal; (d) b - apo - 121 - carotenal - dinitrophenylhydrazone; (e) b - apo - 121 - carotenal - semicarbazone and (f) b -apo-121-carotenal-oxime.

    Production of 2-hydroxy-2,3-dihydrocitral
    95.
    发明专利
    Production of 2-hydroxy-2,3-dihydrocitral 未知

    公开(公告)号：GB1065735A

    公开(公告)日：1967-04-19

    申请号：GB3122364

    申请日：1964-08-04

    Applicant: BASF AG

    Inventor： SCHNEIDER KURT ,  PASEDACH HEINRICH ,  POMMER HORST

    IPC: C07C45/60 ,  C07C47/263 ,  C07D309/06 ,  C11B9/00

    Abstract: 2 - Hydroxy - 2,3 - dihydrocitral is made by reacting a primary or secondary saturated alcohol with 2,2,6 - trimethyl - 6 - ethinyltetrahydropyran at 100-250 DEG C. in the presence of a vinylation catalyst to give the vinyl ether where R is the residue of the alcohol, which is subsequently cleared in an aqueous-acid medium, containing at least a stoichiometric amount of water, at 0-160 DEG C. to give the required compound. The vinylation step is effected in the conventional manner. Preferred alcohols are the mono- or di-hydric aliphatic alcohols having 1-6 carbon atoms which optionally contain an ether linkage. Suitable acids for the hydrolysis step are phosphoric acid, HCl, HI, H2SO4, p-toluene sulphonic acid, strongly acid ion-exchange resins and acid activated bleaching earths and Friedel-Craft catalysts, such as zinc, aluminium and titanium chlorides and boron trifluoride. 2-Hydroxy-2,3-dihydrocitral may be converted to 2-hydroxy-2,3-dihydrocitronellal by selective hydrogenation in the presence of palladium. Examples are provided.

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