Hydrochloric Acid → 4-Methoxybenzoylacetonitrile

HRID 481119

반응식

HRID 481119 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6342Acetonitrile2회HCID 8499Methyl anisateHCID 5360545Sodium

생성물 1

HCID 2333984-Methoxybenzoylacetonitrile

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e14c806467d043fbbb2d9ae5b4457bc2
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653476B2

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