Preparation of e-oxime ethers of phenylglyoxylic esters

Details Preparation of e-oxime ethers of phenylglyoxylic esters Preparation of e-oxime ethers of phenylglyoxylic esters

C - Chemistry, Metallurgy

07

C

C07C 249/08 (2006.01) C07C 51/09 (2006.01) C07C 51/367 (2006.01) C07C 51/60 (2006.01) C07C 63/331 (2006.01) C07C 65/24 (2006.01) C07C 67/22 (2006.01) C07C 69/738 (2006.01) C07C 235/34 (2006.01) C07C 251/48 (2006.01) C07C 253/14 (2006.01) C07C 255/17 (2006.01) C07C 255/40 (2006.01) C07C 317/24 (2006.01)

Patent

CA 2058553

E-oxime ethers of phenyl-glyoxylic esters of the formula I (see formula I) where X and Y are each halogen, C1-C4-alkyl, C1-C4-alkoxy or trifluoromethyl; m is an integer from 0 to 4; n is an integer from 0 to 3; are prepared by a) converting a phenol of the formula II (see formula II) into the phenolate b) mixing this phenolate with a lactone of the formula III (see formula III) c) reacting the mixture in the melt, and d) converting the resulting 2-phenoxymethylbenzoic acid of the formula IV (see formula IV) e) into the corresponding 2-phenoxymethylbenzoyl chloride of the formula V (see formula V) and f) reacting the 2-phenoxymethylbenzoyl chloride V with a cyanide, and g) reacting the resulting 2-phenoxymethylbenzoyl cyanide of the formula VI (see formula VI) with methanol, h) if required cleaving the keto carboxylic ester dimethyl acetal byproduct of the formula VIIb (see formula VIIb) and, if required, subjecting the .alpha.-veto carboxamide byproduct of the formula VIIc (see formula VIIc) to step (g) again or i) reacting an o-phenoxymethylbenzoic ester of the formula Va (see formula Va) where R is alkyl, with dimethyl sulfoxide, mixing the resulting .beta.-keto sulfoxide of the formula VIa (see formula VIa) with a halogenating agent and reacting this mixture with methanol k) and reacting the resulting methyl 2-phenoxymethyl-glyoxylate of the formula VIIa (see formula VIIa) or an acetal of the formula VIIb (see formula VIIb) or a mixture of compounds VIIa and VIIb with O-methylhydroxylamine and treating with an acid.

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