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    3.
    发明专利
    未知

    公开(公告)号：AT203518T

    公开(公告)日：2001-08-15

    申请号：AT98109285

    申请日：1998-05-22

    Applicant: BASF AG

    Inventor： PAUST JOACHIM DR ,  KRIEGL WOLFGANG

    IPC: C07C403/24 ,  C07D493/08 ,  C07F9/50 ,  C07F9/54

    Abstract: Preparation of (3R,3'R)-zeaxanthin (I) comprises: (i) reacting (4R)-4-hydroxy-2,2,6-trimethyl-cyclohexanone (II) with dichloromethyl lithium in an inert solvent at -120 to -40 degrees C and warming the reaction mixture to 20-60 degrees C; (ii) reacting the obtained (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxa-bicyclo (2.2.1) heptane of formula (IV) (in isolated form or directly in the reaction mixture) with acetone or a dialkyl (2-oxo-propyl)-phosphonate; (iii) converting the obtained (4R,6R)-1-(3-oxo-but-1-en-1-yl)-2,2,6-trimethyl-7-oxa-bicyclo (2.2.1) heptane of formula (V) into (4R,6R)-1-(3-hydroxy-3-methylpenta-1,4-dienyl)-2,2,6-trimethyl-7-oxa-b icyclo (2.2.1) heptane (VI) by conventional vinylation (or ethynylation followed by partial hydrogenation); (iv) reacting (VI) with a triaryl phosphine (preferably PPh3) and a strong acid to give a mixture of a C15 triaryl phosphonium salt of formula (III) and the isomer of formula (III'); and (v) subjecting 2 moles of the mixture to a double Wittig olefin synthesis reaction with 2,7-dimethyl-octa-2,4,6-triene-1,8-dial (VIII) to give (I). Ar = aryl (preferably optionally substituted phenyl); and X = 1 equivalent of an anion of a strong acid (preferably Cl, Br or HSO4). The preparation of (I) by step (v) is claimed per se. Also claimed are (IV) and (V) and (III') in mixtures with (III).

    Prepn. of polyene aldehyde derivs. esp. all-E retinal
    5.
    发明专利
    Prepn. of polyene aldehyde derivs. esp. all-E retinal 未知

    公开(公告)号：DE4440286A1

    公开(公告)日：1996-05-15

    申请号：DE4440286

    申请日：1994-11-11

    Applicant: BASF AG

    Inventor： KRAUSE WOLFGANG DR ,  PAUST JOACHIM DR

    IPC: C07C45/29 ,  C07C45/30 ,  C07C403/14

    Abstract: The prepn. of polyene aldehyde derivs. of formula (I) comprises oxidising the corresponding polyene alcohol (II) in the presence of catalytically oxidising ruthenium cpds. or complexes and in the presence of N,N,N-trisubstd. N-oxides of formula (III). R = COOR1, CHO, CH(OR2)2 or a gp. of formula (a). A = CH2 or CHOH; Q = CH2 or CO; R1 = alkyl, aryl, aralkyl, cycloalkyl, (all opt. substd.); R2 = 1-4C alkyl; or R2+R2 = CH2CH2 or CH2CH2CH2 (both opt. substd. with 1-4C alkyl); R3-R5 = 1-6C alkyl, 1-6C alkoxy or 1-6C alkoxyalkyl; or R3+R4 = 5-6 membered heterocycle.

    7.
    发明专利
    未知

    公开(公告)号：DE59300921D1

    公开(公告)日：1995-12-21

    申请号：DE59300921

    申请日：1993-03-09

    Applicant: BASF AG

    Inventor： PAUST JOACHIM DR ,  SIEGEL WOLFGANG DR

    IPC: C07C67/343 ,  C07C69/675

    Abstract: Process for the preparation of esters of beta -hydroxycarboxylic acids of the general formula I … … in which …… R and R denote C1- to C20-alkyl which is optionally substituted by C1- to C8-alkoxy and/or halogen; C3- to C20-alkoxycarbonylalkyl, C2- to C20-alkenyl, C5- to C30-acetylalkenyl, aryl which is optionally mono- to pentasubstituted by C1- to C8-alkyl, C1- to C8-alkoxy and/or halogen; C7- to C20-aralkyl, C7- to C20-aralkenyl, hetaryl, C3- to C20-cycloalkyl, C4- to C20-cycloalkylalkyl or, together, denote a C2- to C8-alkylene chain and R or R denotes hydrogen, … R denotes hydrogen, C1- to C20-alkyl, C2- to C20-alkenyl, aryl which is optionally mono- to pentasubstituted by C1- to C8-alkyl, C1- to C8-alkoxy and/or halogen; C7- to C20-aralkyl, C3- to C20-cycloalkyl or C4- to C20-cycloalkylalkyl, … R denotes C1- to C20-alkyl, C2- to C20-alkenyl, C7- to C20- aralkyl, C3- to C20-cycloalkyl or C4- to C20-cycloalkylalkyl, … by reaction of carbonyl compounds of the general formula II … … in which R and R have the abovementioned meanings, with esters of alpha -bromocarboxylic acids of the general formula III … … in which R and R have the abovementioned meanings, by carrying out the reaction with zinc in dichloromethane at temperatures from 0 to 50 DEG C, and a process for the preparation of esters of alpha -bromozinc-carboxylic acids of the general formula IV … … in which …… R denotes hydrogen, C1- to C20-alkyl, C2- to C20-alkenyl, aryl which is optionally mono- to pentasubstituted by C1- to C8-alkyl, C1- to C8-alkoxy and/or halogen; C7- to C20-aralkyl, C3- to C20-cycloalkyl or C4- to C20-cycloalkylalkyl, … R denotes C1- to C20-alkyl, C4- to C20-alkenyl, C7- to C20- aralkyl, C3- to C20-cycloalkyl or C4- to C20-cycloalkylalkyl, … from esters of alpha -bromocarboxylic acids of the general formula III according to Claim 1, which is characterised in that the reaction with zinc in dichloromethane is carried out at temperatures from 0 to 50 DEG C and the use of dichloromethane for the stable storage of the esters of alpha -bromozinc-carboxylic acids IV.

    9.
    发明专利
    未知

    公开(公告)号：DE4344148A1

    公开(公告)日：1995-08-24

    申请号：DE4344148

    申请日：1993-12-23

    Applicant: BASF AG

    Inventor： JOHN MICHAEL DR ,  PAUST JOACHIM DR

    IPC: C07C51/00 ,  C07C57/03 ,  C07C69/56 ,  C07C403/00 ,  C07C403/20 ,  C07F9/02 ,  C07F9/54 ,  C07C1/34

    Abstract: Process for the preparation of 9-(Z)-retinoic acid from mother liquors from the industrial preparation of C15-triarylphosphonium salts of the formula I in which R to R are an aryl radical and X is halogen or (HSO4) , in an organic solvent, which is characterised in that A. the proportion of 9-(Z)-C15-triarylphosphonium salt in the C15-triarylphosphonium salt isolated from the mother liquor is enriched by treating it with isopropanol in the presence of heat, cooling and separating off the all-(E)-C15-triarylphosphonium salt which crystallises out, B. subjecting the C15-triarylphosphonium salt thus obtained to a Wittig reaction with an alkyl ss-formylcrotonate of the formula and C. hydrolysing the oily retinoic acid ester mixture thus obtained in a C3- to C9-alkanol, preferably in a propanol or butanol, and precipitating the 9-(Z)-retinoic acid obtained, if desired, in crystalline form by addition of methanol, all-(E)-retinoic acid and other retinoic acid isomers remaining in the alkanolic solution.

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