Water → (E)-2-(4-Bromophenyl)-3-cyclohexylacrylic acid

HRID 2103632노트

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HRID 2103632 반응식
C([O:3][C:4](=[O:20])[C:5]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=[CH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.C[O-].[Na+].O.[OH-].[Na+]>CO>[Br:19][C:16]1[CH:15]=[CH:14][C:13](/[C:5](=[CH:6]\[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)/[C:4]([OH:20])=[O:3])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 670844132-(4-Bromo-phenyl)-3-cyclohexyl-acrylic acid ethyl ester

생성물 1

HCID 53471257(E)-2-(4-Bromophenyl)-3-cyclohexylacrylic acid수율 63.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
50 °C

실험 절차

Dissolve E/Z mixture of 2-(4-bromo-phenyl)-3-cyclohexyl-acrylic acid ethyl ester (158.9 g, 472 mmol) in methanol (800 mL) and add the solution to sodium methoxide in methanol (222 mL, 30%). Stir the reaction mixture at 50° C. for 72 h. Add water (17 mL) and 5 N aqueous sodium hydroxide solution (10 mL) and stir at 50° C. until all methyl ester is hydrolyzed (1-4,days). Add water and evaporate the methanol; Add ether (300 mL) and water (200 mL) and adjust the pH to a value of 1 with 1 N HCl. Separate the layers and extract the aqueous layer with ether. Dry the combined organic layers organic phase over sodium sulfate, filter and concentrate. Recrystallization of the residue in EtOAc affords the title compound as a white solid (93.3 g). MS (m/e): 309 (M+H).

후처리

  1. dissolutionDissolve
  2. customAdd water and evaporate the methanol
  3. customSeparate the layers
  4. extractionextract the aqueous layer with ether
  5. dry with materialDry the combined organic layers organic phase over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customRecrystallization of the residue in EtOAc

출처 및 근거

ORD 기록
ord-763078bb8f624cc6b197a0b7c4b3e9a6
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576108B2

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