Hydrochloric Acid → 4-Benzyloxybenzonitrile

HRID 429761

반응식

HRID 429761 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CN(C=O)C.O.C(OCC)(=O)C>[CH2:16]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

생성물 1

HCID 5613714-Benzyloxybenzonitrile수율 93%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-cyanophenol (50 g, 0.42 mol) and potassium carbonate (150 g, 1.1 mol) in DMF (800 ml) was added benzyl bromide (75 ml, 0.63 mol). The reaction mixture was stirred for 2 h at room temperature before filtering off solid and reducing the filtrate in vacuo to give an oil. The solid precipitate was dissolved in water and the pH adjusted to 0.5 using 6.0M hydrochloric acid and extacted into ethyl acetate. The solvent was dried over magnesium sulphate and removed by evaporation in vacuo to give an oil. The two oil products were combined and triturated with diethyl ether/hexane to give a white solid, which was washed with hexane and dried to give the title compound (81 g, 93%). 1H NMR (CDCl3) δ 7.5 (2H, d, 1 8.6 Hz), 7.45-7.30 (5H, br m), 7.0 (2H, d, J 8.6 Hz) and 5.14 (2H, s). MS (ES) m/e 210 [M+H]+.

후처리

  1. filtrationbefore filtering off solid
  2. customto give an oil
  3. dry with materialThe solvent was dried over magnesium sulphate
  4. customremoved by evaporation in vacuo
  5. customto give an oil
  6. customtriturated with diethyl ether/hexane
  7. customto give a white solid, which
  8. washwas washed with hexane
  9. customdried

출처 및 근거

ORD 기록
ord-26987c0b17784e589bc4bcd67eda28af
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319922B1

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