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

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).

1. stirringthe mixture stirred at room temperature over the weekend
2. concentrationThe mixture was then concentrated under vacuum
3. additionby adding 2M hydrochloric acid
4. additionThe mixture was diluted with a little water
5. extractionextracted with DCM (3×20 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-dfaab6075c5a4b078767800ae7be98ab

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895733B2