Hydrochloric Acid → 4-Hydroxy-3-methylbenzonitrile

HRID 1003357노트

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HRID 1003357 반응식
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1.[Cu](C#N)[C:11]#[N:12].O.Cl>CN1C(=O)CCC1.C(OCC)(=O)C>[C:11]([C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1)#[N:12]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 168964-Bromo-2-methylphenolHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 109645604-Hydroxy-3-methylbenzonitrile수율 133.6%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

A mixed solution of 10.89 g (58 mmol) of 4-bromo-cresol and 10.39 g (116 mmol) of copper cyanide in 50 ml of NMP was stirred at 190° C. for 2 hours, followed by the addition of 43 g of FeCl3.6H2O, 65 ml of water and 11 ml of concentrated hydrochloric acid. The resulting mixture was stirred at 80° C. for 30 minutes and was then allowed to cool down. Water and ethyl acetate were added to the reaction mixture, followed by separation into a water layer and an organic layer. The organic layer was dried over Na2SO4, and the solvent was then distilled off under reduced pressure. The residue as purified by column chromatography (chloroform/methanol=40/1), whereby 10.32 g of 4-cyanocresol were obtained as a dark brown oil.

후처리

  1. temperatureto cool down
  2. customfollowed by separation into a water layer
  3. dry with materialThe organic layer was dried over Na2SO4
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe residue as purified by column chromatography (chloroform/methanol=40/1)

출처 및 근거

ORD 기록
ord-38fb365d5a8b4d06abfc58fff0c22699
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046212

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