반응 #530079

반응 방정식

Orcinol monohydrate

sodium hydride

2-trifluoromethylbenzyl chloride

→

title compound

수율 41.1%

5-Methyl-3-(2-trifluoromethylbenzyloxy)phenol

수율 41.1%

용매

N,N-dimethylformamide

N,N-dimethylformarnide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 hours
2. 2
   기타After carefully quenching with water (100 mL)
3. 3
   추출the mixture was extracted with ethyl acetate (3×100 mL)
4. 4
   세척The ethyl acetate solution was washed with brine (2×100 mL)
5. 5
   건조dried over Na2SO4
6. 6
   기타After evaporating the solvent in vacuo
7. 7
   기타the residue was purified by flash column chromatography (3:1 hexane/ethyl acetate)

실험 절차

Orcinol monohydrate (4.30 g, 30 mmol) in N,N-dimethylformarnide (20 mL) was added to a suspension of sodium hydride (1.5 g, 60 mmol) in N,N-dimethylformamide (30 mL), and the mixture was stirred at ambient temperature for 30 minutes. To the above solution was slowly added 2-trifluoromethylbenzyl chloride (5.0 g,25 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at ambient temperature for 3 hours. After carefully quenching with water (100 mL), the mixture was extracted with ethyl acetate (3×100 mL). The ethyl acetate solution was washed with brine (2×100 mL) and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (3:1 hexane/ethyl acetate) to give the title compound as a white solid (2.9 g, 41%). 1H-NMR (300 MHz, CDCl3) δ 7.72 (d, J=7.8 Hz, 1 H), 7.68 (d, J=7.9Hz, 1 H), 7.56 (t, J=7.7 Hz, 1 H), 7.41 (t, J=7.7 Hz, 1 H), 6.39 (s, 1 H), 6.28 (s, 2 H), 5.22 (s, 2 H), 4.79 (s, 1 H), 2.27 (s, 3 H).

출처