Water → 4-(2'-Methoxyphenyl)-3-phenylbutyric acid

HRID 982087

反応式

HRID 982087 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][C:12]#N.[OH-:20].[Na+].[OH2:22]>C(O)CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][C:12]([OH:22])=[O:20]

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 200690144-(2'-Methoxyphenyl)-3-phenylbutanenitrile

生成物 1

HCID 122124054-(2'-Methoxyphenyl)-3-phenylbutyric acid収率 77%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

4-(2'-Methoxyphenyl)-3-phenylbutanenitrile (60.1 g, 239 mmol), from Step 4, was dissolved in 340 mL of ethylene glycol. Sodium hydroxide (67.5 g, 1.69 mol) and 135 mL of water were added and the reaction mixture was heated at reflux temperature for 24 h. The solvent was removed in vacuo and 1 L of water plus 1 L of methylene chloride were added to the residue. The layers were separated and the organic layer discarded. The aqueuous layer was acidified with concentrated aqueous hydrochloric acid and extracted with 3 L of ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 49.8 g (77% yield) of the title compound as an oil; 1H NMR (CDCl3)δ2.6-2.7 (m, 2H), 2.9 (d, 2H), 3.4-3.5 (m, 1H), 3.77 (s, 3H), 6.56 (t, 1H), 6.73 (dd, 1H), 6.80 (d, 1H), 7.0-7.4 (m, 6H).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 24 h
  3. customThe solvent was removed in vacuo and 1 L of water plus 1 L of methylene chloride
  4. additionwere added to the residue
  5. customThe layers were separated
  6. extractionextracted with 3 L 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-c65130a70501495e8c0dfdbbcc02936e
出典データセット
uspto-grants-1991_02
特許番号
US04994486

関連ノート

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