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

HRID 2103632ノート

反応式

HRID 2103632 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-763078bb8f624cc6b197a0b7c4b3e9a6
出典データセット
uspto-grants-2009_08
特許番号
US07576108B2

反応ノート

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