Production of mono-and poly-unsaturated aldehydes or their functional derivatives

    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

    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 polyene aldehydes
    28.
    发明专利

    公开(公告)号:GB1137429A

    公开(公告)日:1968-12-18

    申请号:GB4370566

    申请日:1966-09-30

    Applicant: BASF AG

    Abstract: 1,137,429. Polyene aldehydes. BADISCHE ANILIN- & SODA-FABRIK A.G. 30 Sept., 1966 [2 Oct., 1965], No. 43705/66. Heading C2C. [Also in Division A2] Aldehydes of formula in which the radicals R 1 , from left to right, denote H and CH 3 alternately, the radicals R 2 starting from the -C#C- bond, denote CH 3 and H alternately, m and n are each 0-3 and their sum is at least 1, and the bond indicated by the broken line may be hydrogenated, are prepared by reacting a phosphonium compound of formula in presence of a proton acceptor which will convert it to the ylid and in an organic medium with at least an equimolar amount of a dialdehyde O = HC-(CR 2 = CH)m-C#C-(CH = CR 2 )m-CH = O, X being the 2,2,6-trimethylcyclohex-1-enyl radical.

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