Hydrochloric Acid → 4-Benzyloxybenzonitrile

HRID 429761

Reaktionsgleichung

Reaktionsgleichung von HRID 429761
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 5613714-BenzyloxybenzonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-26987c0b17784e589bc4bcd67eda28af
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319922B1

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