PRODUCTION OF ALPHA-CYANO-TERT-BUTYLACETIC ACID LOWER ALKYL ESTER

• Main Authors: YAMADA YOSHIMI, ENOMOTO MASAYUKI, MAGARA OSAMU
• Format: Patent
• Language: English
• Published: 13.08.1996
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

PURPOSE: To obtain the subject ester useful as a production intermediate for plant blight controlling agents in high efficiency by reacting a specific lower alkyl ester with methylmagnesium halide in the presence of a copper catalyst. CONSTITUTION: This ester is produced by reacting (A) a lower alkyl ester of 2-cyano-3-methyl-2-butenoic acid (e.g. 2-cyano-3-methyl-2-butenoic acid methyl ester) with (B) a methylmagnesium halide (e.g. methylmagnesium chloride) in the presence of (C) a copper catalyst (preferably CuCl, CuBr, CuI, CuCl2 , CuBr2 or CuI2 ) e.g. in THF solvent at 10-60 deg.C for 0.5-10hr. The component A is preferably produced by reacting acetone with a cyanoacetic acid compound (e.g. methyl cyanoacetate) in the presence of a catalyst (e.g. a substituted aniline) using n-hexane as a main solvent.