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

HRID 2263996

反応式

HRID 2263996 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ffcb9308274d4c01b5ea162c5ded78cb
出典データセット
uspto-grants-2010_12
特許番号
US07851626B2

関連ノート

読み込み中…