Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042282A1

    公开(公告)日:1992-07-02

    申请号:DE4042282

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042280A1

    公开(公告)日:1992-07-02

    申请号:DE4042280

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    Process for preparing oxime ethers
    56.
    发明专利

    公开(公告)号:CZ287813B6

    公开(公告)日:2001-02-14

    申请号:CZ160997

    申请日:1995-11-21

    Applicant: BASF AG

    Abstract: The invented process for preparing oxime ethers of the general formula Ia, in which Re3, Re4 are either identical or different and represent alkyl containing 1 to 6 carbon atoms and Re4 furthermore hydrogen and X represents oxygen and NH and A represents CHi3, O-aryl, CHi2-O-aryl, ai1, ai2 or ai3 wherein Re5 to Re7 are identical or different and represent hydrogen, alkyl containing 1 to 4 carbon atoms, aryl and heteroaryl with the proviso than aryl represents phenyl and naphthyl and can be optionally substituted with one to three of the following radicals: halogen, cyano, nitro, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, haloalkyl containing 1 to 4 carbon atoms, haloalkoxy containing 1 to 4 carbon atoms, alkoxyiminoalkyl containing 1 to 4 carbon atoms in both alkoxy and alkyl moieties, aryl, aryloxy, benzyl, benzyloxy, heteroaryl, heteroaryloxy, cycloalkyl containing 3 to 6 carbon atoms, dialkylamino containing 1 to 4 carbon atoms, COi2CHi3, COi2Ci2Hi5, formyl and acetyl that are either identical or different, and heteroaryl represents an optionally substituted unsaturated five- or six-membered heterocycle, which contains one to four nitrogen atoms or one to three nitrogen atoms and one oxygen atom, or a sulfur atom or no nitrogen atom and oxygen atom or a sulfur atom and carries one to three either identical or different substituents being selected from a group comprising halogen, cyano, nitro, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, haloalkyl containing 1 to 4 carbon atoms, haloalkoxy containing 1 to 4 carbon atoms, alkoxyiminoalkyl containing 1 to 4 carbon atoms in both alkoxy and alkyl moieties, aryl, aryloxy, benzyl, benzyloxy, heteroaryl, heteroaryloxy, cycloalkyl containing 3 to 6 carbon atoms, dialkylamino containing 1 to 4 carbon atoms, COi2CHi3, COi2Ci2Hi5, formyl and acetyl, is characterized in that oxime of the general formula IIa, wherein the substituents are as specified above is transferred, optionally in the presence of an organ ic solvent through a base to a corresponding salt and this salt is then brought into reaction with dimethyl carbonate of the general formula III, in which Re3 represents methyl.

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