Water → 6-Methyl-2-nitrophenylpyruvic acid

HRID 564964

반응식

HRID 564964 반응식
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[C:12](OCC)(=[O:18])[C:13]([O:15]CC)=[O:14].CC(C)([O-])C.[K+].O>C(O)C>[CH3:11][C:3]1[C:2]([CH2:1][C:12](=[O:18])[C:13]([OH:15])=[O:14])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 7268Diethyl OxalateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 211942326-Methyl-2-nitrophenylpyruvic acid수율 46.6%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of 15.1 g (0.10 mol) of 2-methyl-3-nitrotoluene and 14.6 g (0.10 mol) of diethyl oxalate in 10 ml of ethanol was added to a solution of 11.2 g (0.10 mol) of potassium tert-butoxide in 50 ml of ethanol. After stirring at room temperature for 1.5 hour, the reaction mixture was refluxed for 1.5 hour. After 60 ml of water was added to the reaction mixture, the mixture was refluxed for further an hour. After cooling, ice water was poured onto the reaction mixture followed by washing twice with ethyl acetate. The aqueous layer was acidified with conc. hydrochloric acid and then extracted three times with chloroform. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 10.4 g (46.6%) of the desired 6-methyl-2-nitrophenylpyruvic acid.

후처리

  1. temperaturethe reaction mixture was refluxed for 1.5 hour
  2. temperaturethe mixture was refluxed for further an hour
  3. temperatureAfter cooling
  4. washby washing twice with ethyl acetate
  5. extractionextracted three times with chloroform
  6. washThe combined extracts were washed with water
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-d9452b5547c34f5a8b5d3e9708274a1b
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169107A

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