Acetone → Methyl 3-methoxy-4-nitrobenzoate

Participants

Reaction Steps

A 5-L, 3-necked, round-bottomed flask fitted with an overhead stirrer and a 250 mL addition funnel was charged with 3-hydroxy-4-nitrobenzoic acid (122 g, 0.66 mol), acetone (reagent grade, 1.5 L) and powdered K2CO3 (185 g). To this stirred suspension dimethylsulfate (127 mL) was added drop-wise. The suspension was stirred at room temperature for 18 h and filtered. The filtrate was concentrated under reduced pressure to about half the volume (ca 750 mL), transferred to a 3-L beaker and water (1-L) was added with stirring. The precipitated product was collected by filtration and dried in vacuum to obtain the title compound 32 as a white crystalline solid mp 87-88° C. 1H NMR (400 MHz, CDCl3) δ: 7.77 (d, 1H), 7.68 (d, 1H), 7.63 (d, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (ES) m/z212.1 (MH)+.

Provenance & Evidence