Hydrochloric Acid → 3-tert-Butyl-5-cyanobenzoic acid

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Reaction Steps

To a solution of methyl 3-tert-butyl-5-cyanobenzoate (8.8 g, 0.0360 mol) in MeOH (76 mL) was added a solution of NaOH (2.0 g, 0.050 mol) in water (15 mL). The mixture was allowed to stir at rt for 2.5 h and then acidified with 1N HCl. The mixture was concentrated to remove methanol and the residue was extracted with EtOAc. The organic solutions were combined, washed with 1NHCl and brine, dried over Na2SO4, filtered, and concentrated to a small volume. Hexane was added and the product precipitated. The solid was filtered, washed with hexanes and dried to give 3-tert-butyl-5-cyanobenzoic acid (9.1 g, 73%). 1H NMR (400 MHz, d6-DMSO) δ: 8.19 (m, 1H), 8.13 (m, 1H), 8.10 (m, 1H), and 1.32 (s, 9H). LCMS: ES− 202.2.

Provenance & Evidence