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

HRID 39425

반응식

HRID 39425 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 594384852-Cyclopropyl-4-(trifluoromethyl)benzoic acid수율 43.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-513a2865dc3247a8bbc54ea1d3089d65
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524909B2

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