Lithium Hydroxide → 3-(2-Cyanopropan-2-yl)benzoic acid

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Reaction Steps

A solution of methyl 3-(2-cyanopropan-2-yl)benzoate 2 (72 g, 5.9 mmol) in THF (900 mL), MeOH (300 mL) and water 300 (mL) was treated with lithium hydroxide (47.6 g, 1.13 mol). The mixture was stirred overnight at rt. Concentrated to ±300 mL in vacuo and the resulting solution was acidified with 1N HCl solution. The resulting white precipitate was collected, washed with water and dried. Purification by column chromatography (5% methanol in CH2Cl2) gave pure 3-(2-cyanopropan-2-yl)benzoic acid 3 (20.7 g, 31%). 1H-NMR (400 MHz, CDCl3) 1.78 (s, 6H), (t, J=7.5 Hz, 1H), 7.80 (m, 1H), 8.09 (m, 1H), 8.20 (m, 1H).

Provenance & Evidence