Ethanol → 3-Ethoxy-3-oxo-2-phenylpropanoic acid

HRID 36900

반응식

HRID 36900 반응식
[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:18](O)[CH3:19]>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH2:18][CH3:19])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

생성물 1

HCID 27299033-Ethoxy-3-oxo-2-phenylpropanoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 3283Diethyl Ether용매

실험 절차

Phenylmalonic acid (13.5 g, 0.07 mol) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was evaporated under reduced pressure to remove any residual thionyl chloride. The oily residue was redissolved in dry ether (40 mL), the solution was treated with ethanol (0.075 mol, 4.1 mL) and refluxed for 2 hours. The reaction mixture was cooled to room temperature and washed with water. The organic layer was extracted with saturated solution of sodium bicarbonate until alkaline. The combined extracts were washed with ether and the aqueous layer was acidified with 5N HCl to pH 1. The precipitated oil was extracted with CH2Cl2 (50 mL×3). The combined extracts were washed with water (50 mL×4) and dried over anhydrous MgSO4. The oily product crystallized on standing.

후처리

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. customThe clear solution was evaporated under reduced pressure
  3. customto remove any residual thionyl chloride
  4. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  5. temperaturerefluxed for 2 hours
  6. washwashed with water
  7. extractionThe organic layer was extracted with saturated solution of sodium bicarbonate until alkaline
  8. washThe combined extracts were washed with ether
  9. extractionThe precipitated oil was extracted with CH2Cl2 (50 mL×3)
  10. washThe combined extracts were washed with water (50 mL×4)
  11. dry with materialdried over anhydrous MgSO4
  12. customThe oily product crystallized

출처 및 근거

ORD 기록
ord-d0d304e48bc64f40b143545cd4b9d69b
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418244

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