2,6-Dimethoxybenzonitrile → 2,6-Dihydroxybenzonitrile

HRID 2282067

반응식

HRID 2282067 반응식
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[C:11]=1[C:12]#[N:13]>O>[OH:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=1[C:12]#[N:13]

참가 물질

4

반응물 2

HCID 856482,6-DimethoxybenzonitrileHCID 10176127Pyridinium chloride2회

생성물 1

HCID 937912,6-Dihydroxybenzonitrile수율 60%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
210 °C

실험 절차

Another potential method utilizes pyridine hydrochloride in place of the boron tribromide. Into a 500 mL 3-neck round bottom flask equipped with stir bar, nitrogen inlet and condenser was charged 2,6-dimethoxybenzonitrile (15.0 g, 91.9 mmol), followed by pyridine hydrochloride (150 g). The mixture was heated to 210° C. for 2 hours and allowed to cool to room temperature. Water was then added to the flask to dissolve the solidified mixture. The aqueous layer was then extracted with ethyl acetate (150 mL) 3 times. The combined organic layer was dried under anhydrous sodium sulfate, and the solvent was removed to yield 7.44 g (60.0%) of a light pink solid, m.p.: 202.8-204.8° C. 1H-NMR (DMSO-d6): 6.39-6.41 (d, 2H, Ar—H), 7.20-7.24 (t, 1H), 10.78 (s, 2H, Ar—O—H).

후처리

  1. customInto a 500 mL 3-neck round bottom flask equipped
  2. temperatureto cool to room temperature
  3. dissolutionto dissolve the solidified mixture
  4. extractionThe aqueous layer was then extracted with ethyl acetate (150 mL) 3 times
  5. customThe combined organic layer was dried under anhydrous sodium sulfate
  6. customthe solvent was removed

출처 및 근거

ORD 기록
ord-d896ef3866aa493dbffc2253c29e1818
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139696B1

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