Sodium Hydroxide → 2-Cyclopropyl-4-(trifluoromethyl)benzoic acid

HRID 39425

反応式

HRID 39425 の反応式
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH:14]1[CH2:16][CH2:15]1.[OH-].[Na+]>C(O)C>[CH:14]1([C:5]2[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:4]=2[C:3]([OH:17])=[O:2])[CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59438487Methyl 2-cyclopropyl-4-(trifluoromethyl)benzoate

生成物 1

HCID 594384852-Cyclopropyl-4-(trifluoromethyl)benzoic acid収率 43.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 485 mg (1.986 mmol) 2-cyclopropyl-4-trifluoromethyl-benzoic acid methyl ester in 8 ml ethanol at room temperature, was added 1.99 ml (3.972 mmol) 2N NaOH. The mixture was heated in an 80° C. oil bath for 30 minutes. The solution was cooled to room temperature and the ethanol was evaporated. The residue was diluted with water, acidified with 2N HCl to pH 2 and dichloromethane was added. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (eluent: heptane/ethyl acetate 0 to 100%) to provide 0.197 g (27%) of the title compound as a light yellow solid. MS (m/e): 229.0 (M−H).

後処理

  1. temperatureThe solution was cooled to room temperature
  2. customthe ethanol was evaporated
  3. additionThe residue was diluted with water
  4. additionwas added
  5. extractionThe aqueous phase was extracted twice with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on silica gel (eluent: heptane/ethyl acetate 0 to 100%)

出典と根拠

ORDレコード
ord-513a2865dc3247a8bbc54ea1d3089d65
出典データセット
uspto-grants-2013_09
特許番号
US08524909B2

関連ノート

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