Methyl iodide → Methyl 5-cyano-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl-2-hydroxy-5-cyano-benzoate (2.g, 5.6 mmol), K2CO3 (4.68 g, 16.8 mmol) in acetone (50 ml) was added methyl iodide (0.7 ml, 5.6 mmol). The reaction was then heated at 65° C. overnight resulting in formation of a solid which was filtered off whilst hot and washed with acetone to give 5-cyano-2-methoxy-benzoic acid methyl ester (0.45 g). The crude product was dissolved in THF (5 ml) and then treated with LiOH (0.108 g 0.26 mmol) in water (5 ml) and stirred at room temperature overnight. The reaction was acidified with 2M HCl and extracted EtOAc (×2). The organic portion dried (MgSO4) and reduced in vacuo to give 5-cyano-2-methoxy-benzoic acid (0.277 g). (LC/MS Acidic: Rt 2.92, [M+H]+ 178).

Provenance & Evidence