Water → 6-Methyl-2-nitrophenylpyruvic acid

HRID 1067752

反応式

HRID 1067752 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 211942326-Methyl-2-nitrophenylpyruvic acid収率 46.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb9f67a046554066a91d1582abdec0fc
出典データセット
uspto-grants-2001_06
特許番号
US06248772B1

関連ノート

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