PRODUCTION OF PHENOXY SUBSTITUTED ESTER
Compounds of the formula I I where R1 is where A is C1-C4-alkyl, phenyl or C7-C12-aralkyl and l is 0 or 1, R2 is C1-C4-alkyl, n is 0, 1, 2 or 3, m is 1, 2 or 3 and Y is hydrogen, fluorine, chlorine, bromine, C1-C3-alkyl, C1-C3-alkoxy, trifluoromethyl, phenyl or phenoxy, and, where m is greater than...
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Zusammenfassung: | Compounds of the formula I I where R1 is where A is C1-C4-alkyl, phenyl or C7-C12-aralkyl and l is 0 or 1, R2 is C1-C4-alkyl, n is 0, 1, 2 or 3, m is 1, 2 or 3 and Y is hydrogen, fluorine, chlorine, bromine, C1-C3-alkyl, C1-C3-alkoxy, trifluoromethyl, phenyl or phenoxy, and, where m is greater than 1, the individual atoms or groups Y are identical or different, are prepared by a process in which, in a first stage, a diester of the formula II II is hydrolyzed with one equivalent of an aqueous alkali metal hydroxide to give the alcohol of the formula IIIa IIIa in a second stage this alcohol is converted with a halo-generating agent or a sulfonyl chloride or bromide into a compound of the formula IIIb IIIb where X is a necleophilically displaceable leaving group, such as chlorine, bromine, mesyl or tosyl, and then, in a third stage, the compound IIIb is reacted with a phenolate of the formula IV IV where Y and m have the abovementioned meanings, in the presence of an aprotic solvent to give compound I. Furthermore, diesters of the formula II and a process for their preparation are provided, the said diesters being prepared by reacting a lactone of the formula V V with a Grignard compound VI R1MgZ VI where Z is chlorine or bromine, in a nonpolar organic solvent, from 2 to 3 moles of the Grignard compound being used per mole of lactone, and the reaction mixture then being treated with from 2 to 3 moles of anhydride VII VII per mole of lactone. |
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