반응 #48216

반응 방정식

hydrochloric acid

Sodium hydride

4-fluoro-3-trifluoromethyl benzoic acid

benzyl alcohol

→

4-Benzyloxy-3-trifluoromethyl-benzoic Acid

용매

water

DMSO

반응 조건

후처리

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

실험 절차

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]+).

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