Malonic Acid → 3-{2-Methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid

HRID 4751

반응식

HRID 4751 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([OH:20])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:4]=1C=O.[C:21](O)(=O)[CH2:22][C:23]([OH:25])=[O:24].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([OH:20])([C:12]([F:14])([F:15])[F:13])[C:16]([F:18])([F:17])[F:19])[CH:8]=[CH:7][C:4]=1[CH:21]=[CH:22][C:23]([OH:25])=[O:24]

참가 물질

5

반응물 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 140766522-Methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzaldehyde

생성물 1

HCID 545552723-{2-Methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid수율 61%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 15 g (0.05 mole) 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzaldehyde in 50 ml of pyridine are added 11 g (0.11 mole) of malonic acid and 1 g of piperidine. The solution is stirred and gradually heated to 80°. Heating and stirring are continued for 1 hour at 80°. The solution is then heated at reflux for an additional 3 hours, cooled, and evaporated at reduced pressure to obtain a residual oil which is extracted into ether. The resulting ether solution is washed with water and 1N hydrochloric acid, dried with anhydrous magnesium sulfate, filtered, and evaporated at reduced pressure to obtain a residual solid which is recrystallized from chlorobutane/hexane mixed solvent to give 10.5 g of 3-{2 -methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid having a melting point of 138°-140°.

후처리

  1. temperaturegradually heated to 80°
  2. temperatureHeating
  3. stirringstirring
  4. temperatureThe solution is then heated
  5. temperatureat reflux for an additional 3 hours
  6. temperaturecooled
  7. customevaporated at reduced pressure
  8. customto obtain a residual oil which
  9. extractionis extracted into ether
  10. washThe resulting ether solution is washed with water and 1N hydrochloric acid
  11. dry with materialdried with anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customevaporated at reduced pressure
  14. customto obtain a residual solid which
  15. customis recrystallized from chlorobutane/hexane mixed solvent

출처 및 근거

ORD 기록
ord-ec0779edb24c45fe9d209facc9386718
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727180

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