Water → 4-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid

HRID 54117

反応式

HRID 54117 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:14]#N.[OH-:22].[Na+].[OH2:24]>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:14]([OH:24])=[O:22]

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 199611014-(2',3'-Dimethoxyphenyl)-3-phenylbutanenitrile

生成物 1

HCID 124785434-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid収率 98%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-(2',3'-Dimethoxyphenyl)-3-phenylbutanenitrile (20 g, 71 mmol), from Step 4, was dissolved in 1.5L of ethanol. Sodium hydroxide (20 g, 0.5 mol) and 200 mL of water were added and the reaction mixture was heated at reflux temperature for 24 h. The solvent was removed in vacuo and 1L of water plus 1L of methylene chloride were added to the residue. The layers were separated and the organic layer discarded. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with 3L of ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 21 g (98% yield) of the title compound as an oil; 1H NMR (CDCl3) δ: 2.6-2.7 (m, 2H), 2.9 (d, 2H), 3.4-3.5 (m, 1H), 3.72 (s, 3H), 3.82 (s, 3H), 6.6 (dd, 1H), 6.73 (dd, 1H), 6.88 (t, 1H), 7.1-7.3 (m, 5H).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 24 h
  3. customThe solvent was removed in vacuo and 1L of water plus 1L of methylene chloride
  4. additionwere added to the residue
  5. customThe layers were separated
  6. extractionextracted with 3L of ethyl acetate
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d16d100785e340b78a994f8fa9a321c5
出典データセット
uspto-grants-1997_04
特許番号
US05621133

関連ノート

読み込み中…