Reacción #48216

Ecuación de reacción

hydrochloric acid

Sodium hydride

4-fluoro-3-trifluoromethyl benzoic acid

benzyl alcohol

→

4-Benzyloxy-3-trifluoromethyl-benzoic Acid

Disolventes

water

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe white precipitate was filtered off
2. 2
   workup.DISSOLUTIONdissolved in ethyl acetate (ca 50 mL)
3. 3
   Secadodried over sodium sulphate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was recrystallised from ethyl acetate/hexane

Procedimiento

Sodium hydride (60%, 1.80 g, 45 mmol) was added to a solution of 4-fluoro-3-trifluoromethyl benzoic acid (4.162 g, 20 mmol) and benzyl alcohol (3.25 g, 30 mmol) in DMSO (50 mL). The mixture was stirred overnight at room temperature, poured into water (50 mL) and acidified with concentrated hydrochloric acid. The white precipitate was filtered off, dissolved in ethyl acetate (ca 50 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallised from ethyl acetate/hexane. Yield: 4.252 g (72%). 1H-NMR (400 MHz, CDCl3) δ=5.37 (s, 2H), 7.32-7.48 (m, 6H), 8.12 (d, J=2.0 Hz, 1H), 8.18 (dd, J=8.6, 2.0 Hz, 1H), 13.16 (br s, 1H, —COOH). LRMS (FAB+): 91.1 (100), 297.1 (18, [M+H]+).

Fuente