Tetrahydrofuran → 4-[(2,2,2-TRIFLUOROETHOXY)METHYL]BENZOIC ACID

Participants

Reaction Steps

Methyl 4-[(2,2,2-trifluoroethoxy)methyl]benzoate (Intermediate 249, 1.05 g, 4.23 mmol) was dissolved in MeOH (10 mL), 2M aq. sodium hydroxide (6.4 mL, 12.69 mmol) was added and the mixture was stirred at room temperature for 3 h. THF (2 mL) was then added and the mixture stirred at room temperature over the weekend. The mixture was then concentrated under vacuum and the residue acidified by adding 2M hydrochloric acid. The mixture was diluted with a little water and extracted with DCM (3×20 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford the title compound as a white solid (0.974 g, 98%). 1H NMR (500 MHZ, CDCl3) δ ppm 8.14 (2H, d), 7.49 (2H, d), 4.79 (2H, s) and 3.91 (2H, q).

Provenance & Evidence