Ethanol → Ethyl 2-ethoxy-4-(trifluoromethyl)benzoate

HRID 2263996

반응식

HRID 2263996 반응식
[OH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH3:22].[CH2:24](O)[CH3:25]>>[CH2:24]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:2]=1[O:1][CH2:21][CH3:22])[CH3:25]

참가 물질

5

반응물 4

HCID 702EthanolHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1645782-Hydroxy-4-(trifluoromethyl)benzoic acid

생성물 1

HCID 66857656Ethyl 2-ethoxy-4-(trifluoromethyl)benzoate수율 74%

실험 절차

To a solution of 2-hydroxy-4-trifluoromethyl-benzoic acid (5 g, 24.258 mmol, Matrix Scientific) in ethanol (50 mL) were added potassium carbonate (8.38 g, 60.645 mmol) and ethyl iodide (7.68 mL, 97.032 mmol). The reaction mixture was heated at gentle reflux for 4 h then concentrated in vacuo. The residue was taken in petroleum ether and water, and the layers were separated. The product was extracted with petroleum ether (1×). The organic layers were washed with brine (1×), dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the crude residue by flash chromatography (40 g of silica gel, eluting with 10% ethyl acetate in hexane) gave 2-ethoxy-4-trifluoromethyl-benzoic acid ethyl ester as colorless oil (4.68 g, 74%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 4 h
  3. concentrationthen concentrated in vacuo
  4. customwater, and the layers were separated
  5. extractionThe product was extracted with petroleum ether (1×)
  6. washThe organic layers were washed with brine (1×)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude residue
  11. washby flash chromatography (40 g of silica gel, eluting with 10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-ffcb9308274d4c01b5ea162c5ded78cb
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851626B2

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