Insight into solid-liquid phase transfer catalyzed synthesis of Mecoprop ester using K2CO3 as base and development of new kinetic model involving liquid product and two solid co-products

• Published in: Journal of chemical sciences (Bangalore, India) India), 2017, Vol.129 (11), p.1677-1685
• Main Authors: Yadav, Ganapati D, Deshmukh, Gunjan P
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Regular Article
• ISSN: 0974-3626; 0973-7103
• DOI: 10.1007/s12039-017-1368-1

2-Methyl-4-chlorophenoxy propionic acid (Mecoprop) is a widely used household herbicide. In the current work, a simple synthetic method is developed for Mecoprop methyl ester using solid-liquid phase transfer catalysis (S-L PTC) with K 2 CO 3 as mild base and toluene as solvent. Conversion of 95% was achieved with 100% selectivity for Mecoprop ester at 100 ∘ C . Simple isolation process was employed to recover the product from the reaction mixture. A reaction mechanism was proposed and new kinetic model developed involving one liquid and two solid co-products. The activation energy for the reaction was calculated. This is the first example of its kind being reported vis-à-vis kinetics and mechanism. Graphical Abstract Solid-liquid phase transfer catalyzed (S-L PTC) O-alkylation of 4-chloro-2-methyl phenol is done at relatively mild conditions to form methyl 2-(4-chloro-2-methylphenoxy) propionate (Mecoprop methyl ester). New insight on reaction mechanism and kinetics is presented.