PRODUCTION OF 2-(HALOMETHYL)PHENYLACETIC ACID ESTERS

PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for a cephalosporin-based antibiotic and an intermediate for an agricultural fungicide in high yield by reacting a 3-isochromanone with a hydrogen halide and an alcohol. SOLUTION: A 3-isochromanone of formula I (R is H, a...

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Bibliographic Details
Main Authors ONO YUKIO, HIRAI KENJI, MASUDA KATSUYUKI, TAKAO YOSHIHIRO, MATSUZAWA MASAFUMI
Format Patent
LanguageEnglish
Published 22.12.1997
Edition6
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for a cephalosporin-based antibiotic and an intermediate for an agricultural fungicide in high yield by reacting a 3-isochromanone with a hydrogen halide and an alcohol. SOLUTION: A 3-isochromanone of formula I (R is H, a halogen, a 1-6C alkyl or 1-6C alkyloxy) is reacted with a hydrogen halide and an alcohol of the formula R OH (R is a 1-6C alkyl) at -20 to 80 deg.C to give a 2-(halomethyl phenylacetic acetic acid ester of formula II (X is a halogen). The compound of formula I is reacted with a halomethyl alkyl ether and reacted with the alcohol in the presence of a base to give also the compound of formula II. Hydrogen chloride or hydrogen bromide is preferable as the hydrogen halide. The amount of the hydrogen halide used is 1-30mol equivalent based on the raw material substrate. Methyl alcohol is preferable as the alcohol. The compound of formula II is obtained in excellent selectivity under a mild condition.
Bibliography:Application Number: JP19960147110