Ethyl 2-(4-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoate → 2-[(2H-1,3-Benzodioxol-5-yl)oxy]-6-(4-methoxyphenoxy)benzoic acid

HRID 1600853

반응식

HRID 1600853 반응식
[OH-].[Na+].CCO.[CH3:6][O:7][C:8]1[CH:35]=[CH:34][C:11]([O:12][C:13]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][C:28]4[O:31][CH2:32][O:33][C:27]=4[CH:26]=3)[C:14]=2[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1>>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][C:28]4[O:31][CH2:32][O:33][C:27]=4[CH:26]=3)[C:14]=2[C:15]([OH:17])=[O:16])=[CH:34][CH:35]=1

참가 물질

3

반응물 2

HCID 15540784Ethyl 2-(4-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoateHCID 23692425Sodium hydroxide ethanol

생성물 1

HCID 158723412-[(2H-1,3-Benzodioxol-5-yl)oxy]-6-(4-methoxyphenoxy)benzoic acid수율 80.9%

실험 절차

NaOH/EtOH (0.5 M) was added to ethyl 2-(4-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoate (175 mg, 0.429 mmol) at 25° C. The mixture (solid and solution) was heated under reflux for 20 hr. until TLC indicated the absence of starting material and the formation of a polar material. The solvent was evaporated and the residue was diluted with H2O (7 ml, pH≈7.5) and extracted with EtOAc (2×7ml) to give 132 mg 2-(4-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoic acid as a yellow foam which was recrystallized from MeOH/H2O (twice) to give 102 mg of colorless needles, m.p. 164-165° C.

후처리

  1. temperatureThe mixture (solid and solution) was heated
  2. temperatureunder reflux for 20 hr
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with H2O (7 ml, pH≈7.5)
  5. extractionextracted with EtOAc (2×7ml)

출처 및 근거

ORD 기록
ord-d91987c887834d1fa192ff5931742300
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977117

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