反応 #48216

反応方程式

hydrochloric acid

Sodium hydride

4-fluoro-3-trifluoromethyl benzoic acid

benzyl alcohol

→

4-Benzyloxy-3-trifluoromethyl-benzoic Acid

溶媒

water

DMSO

反応条件

後処理

1. 1
   ろ過The white precipitate was filtered off
2. 2
   workup.DISSOLUTIONdissolved in ethyl acetate (ca 50 mL)
3. 3
   乾燥dried over sodium sulphate
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was recrystallised from ethyl acetate/hexane

実験手順

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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