Hydrochloric Acid → 4-Methoxybenzoylacetonitrile

HRID 481119

反応式

HRID 481119 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[CH:5][CH:4]=1.[Na].Cl.[C:15](#[N:17])[CH3:16]>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH2:16][C:15]#[N:17])=[O:9])=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6342Acetonitrile2 回HCID 8499Methyl anisateHCID 5360545Sodium

生成物 1

HCID 2333984-Methoxybenzoylacetonitrile

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

To a solution of methyl 4-methoxybenzoate (7.2 kg) in dimethyl sulfoxide (21.6 L) were added sodium methoide (3.046 kg) and acetonitrile (2.135 kg) and the mixture was stirred at 110° C. for 2 hours. Then, water (10.83 L) was added dropwise thereto at 15° C. or lower and further acetonitrile (14.4L) was added to the mixture. Then, 6 N HCl was added thereto to adjust to pH 7.9 and the mixture was extracted with ethyl acetate (72L). The aqueous layer was further extracted with ethyl acetate (36.32 L). The organic layers were combined and concentrated until the content became 17.39 kg. Methanol (17.84 L) was added thereto and water (17.84 L) was added dropwise. Then, the mixture was stirred at 5° C. for 1 hours and crystals deposited were filtered off and washed with methanol-water (1:1) to obtain the titled compound '6.40 kg, 82.7 g). 1H-NMR (CDCl3) δ:3.90 (3H, s), 4.03 (2H, s), 6.98 (2H, d, J=11.25 Hz), 7.50 (2H, d, J=11.25 Hz).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (72L)
  2. extractionThe aqueous layer was further extracted with ethyl acetate (36.32 L)
  3. concentrationconcentrated until the content
  4. additionMethanol (17.84 L) was added
  5. additionwater (17.84 L) was added dropwise
  6. stirringThen, the mixture was stirred at 5° C. for 1 hours
  7. filtrationcrystals deposited were filtered off
  8. washwashed with methanol-water (1:1)

出典と根拠

ORDレコード
ord-e14c806467d043fbbb2d9ae5b4457bc2
出典データセット
uspto-grants-2003_11
特許番号
US06653476B2

関連ノート

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