Lithium Hydroxide → HCID 67324495, compound

Participants

Reaction Conditions

Reaction Steps

The compound methyl 3-cyano-5-ethylbenzoate (270 mg, 1.42 mmol) was dissolved in THF—H2O (7:3 v/v, 10 mL), solution was cooled to 0° C. and LiOH (59 mg, 1.42 mmol) was added. The reaction mixture was allowed to come to room temperature and stirred for 3 h (monitored by TLC; petroleum ether/EtOAc 1:1). Solvent THF was removed under reduced pressure and the aqueous layer was washed with EtOAc to remove the non-polar impurities. The pH of the aqueous layer was adjusted to 2-3 using 1.5N HCl. The product was extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 3-cyano-5-ethylbenzoic acid (200 mg, yield 80%), which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.23 (m, 1H), 8.17 (m, 1H), 7.74 (m, 1H), 2.81 (q, J=7.6 Hz, 2H), 1.32 (t, J=7.6 Hz, 3H).

Provenance & Evidence