Sodium hydride → 5-Methyl-3-(2-trifluoromethylbenzyloxy)phenol

HRID 442897

반응식

HRID 442897 반응식
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[H-].[Na+].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Cl>CN(C)C=O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[C:14]([F:13])([F:23])[F:24])[CH:3]=[C:4]([OH:5])[CH:6]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 3083941Resorcinol, 5-methyl-, monohydrate

생성물 1

HCID 536610605-Methyl-3-(2-trifluoromethylbenzyloxy)phenol수율 41.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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).

후처리

  1. stirringThe mixture was stirred at ambient temperature for 3 hours
  2. customAfter carefully quenching with water (100 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  4. washThe ethyl acetate solution was washed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter evaporating the solvent in vacuo
  7. customthe residue was purified by flash column chromatography (3:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-2f7c739d292f412682ae2342b9f6a2f4
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

연결된 노트

불러오는 중…