Sodium Hydroxide → 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid

HRID 1596802

반응식

HRID 1596802 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19]CC)=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 21703105Ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylate

생성물 1

HCID 155384031-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
5 °C

실험 절차

Crude ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylat (30 g) is dissolved in EtOH (96%, 150 ml) and aqueous 2N NaOH (150 ml). The solution is refluxed for 1 hour. ½ of the volume is removed in vacuo. The aqueous phase is extracted with EtOAc (2×100 ml). The aqueous phase is made acidic (pH=1, conc. HCl) and after cooling to 5° C. the white crystals are filtered off. Yield 16 g. Overall yield is 66% starting from 5-ethoxycarbonylphthalide. Mp 187-190° C.

후처리

  1. temperatureThe solution is refluxed for 1 hour
  2. custom½ of the volume is removed in vacuo
  3. extractionThe aqueous phase is extracted with EtOAc (2×100 ml)
  4. filtrationare filtered off

출처 및 근거

ORD 기록
ord-972e933fb03a43018afe59087d33f334
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291689B1

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