Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile

HRID 1951375ノート

反応式

HRID 1951375 の反応式
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[CH3:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17].C(O)(=O)C.N1CCCCC1>ClCCl>[C:16]([C:15]([C:14](=[O:19])[CH3:13])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])(=[O:18])[CH3:17]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 166592514-Formyl-3-methoxybenzonitrile

生成物 1

HCID 591869164-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

21 g (130 mmol) of 4-formyl-3-methoxybenzonitrile, 14.7 ml (143 mmol) of 2,4-pentanedione, 11.2 ml (195 mmol) of acetic acid and 2.6 ml (26 mmol) of piperidine in 400 ml of dry dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from diethyl ether. 23.2 g (92% of theory) of the title compound are obtained as a pale brown solid.

後処理

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-7902c796ca9e4929bc8233ebfb11da6c
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

反応ノート

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