4-Acetylbiphenyl → Ethyl 3-oxo-3-(4-phenylphenyl)propanoate

HRID 1820852

反応式

HRID 1820852 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:18]([O:20][C:21](=O)[O:22]CC)[CH3:19]>>[C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH2:2][C:21]([O:20][CH2:18][CH3:19])=[O:22])=[CH:5][CH:6]=1

参加物

4

反応物 3

HCID 71134-AcetylbiphenylHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

生成物 1

HCID 2756708Ethyl 3-oxo-3-(4-phenylphenyl)propanoate

反応条件

温度
80 °C

実験手順

14.7 g (75.0 mmol) of 4-acetylbiphenyl is dissolved in 150 mL of diethylcarbonate. Under protective gas, a total of 6.50 g (150 mmol) sodium hydride in oil (55%) is added batchwise at 0° C. The mixture is kept for 5 minutes at 0° C., then stirred for 2 hours at 80° C. After cooling, the mixture is poured onto water and extracted with methylene chloride; the organic phase is washed with water and finally dried over sodium sulfate. The solvent is eliminated, the residue is suspended in water and neutralized with 1N hydrochloric acid. The aqueous phase is extracted with diethyl ether, the organic phase is dried over sodium sulfate, and finally the solvent is eliminated. Lastly the residue is recrystallized from petroleum ether and the product is dried in vacuo at 50° C. Yield: 15.3 g (76% of theory); Rf value: 0.60 (silica gel, petroleum ether/ethyl acetate=5:2); m.p. 75° C.-77° C.; C17H16O3; EII mass spectrum: m/z=269 [M+H]+.

後処理

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto water
  3. extractionextracted with methylene chloride
  4. washthe organic phase is washed with water
  5. dry with materialfinally dried over sodium sulfate
  6. extractionThe aqueous phase is extracted with diethyl ether
  7. dry with materialthe organic phase is dried over sodium sulfate
  8. customLastly the residue is recrystallized from petroleum ether
  9. customthe product is dried in vacuo at 50° C

出典と根拠

ORDレコード
ord-c178a8d09327411d82e92ac88faa8d7a
出典データセット
uspto-grants-2009_10
特許番号
US07605176B2

関連ノート

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