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

HRID 233381

반응식

HRID 233381 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4-(2',3'-Dimethoxyphenyl)-3-phenylbutanenitrile (20 g, 71 mmol), from Step 4, was dissolved in 1.5 L 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 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 aqueous layer was acidified with concentrated 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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-de20507ff9aa4d49828923c54aec8c2b
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591884

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