公开(公告)号：GB1079217A

公开(公告)日：1967-08-16

申请号：GB4822864

申请日：1964-11-27

Applicant: BASF AG

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

IPC: C07C45/72 ,  C07C47/20 ,  C07F9/535

Abstract: Polyunsaturated aldehydes are produced by reacting an aldehyde with an ylenal of formula 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 in which R4 may be a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl radical. The radical R4 may contain, for example, the group 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.