4-Hydroxy-3,5-bis(t-butyl)benzaldoxime → Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-

HRID 843999

Reaktionsgleichung

Reaktionsgleichung von HRID 843999
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[CH:8]=[N:9]O)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C.C(OCC)C>[C:15]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]=1[OH:14])[C:8]#[N:9])([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 2

HCID 3285904-Hydroxy-3,5-bis(t-butyl)benzaldoximeHCID 516892Sodium Bicarbonate

Produkt 1

HCID 137274Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-Ausbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3,5-Di-tert-butyl-4-hydroxy-benzaldehyde oxime (3.0 grams, 8.4 mmole) in acetic anhydride (6 ml) was was refluxed for 2 hours. The mixture was cooled to 0° C. and saturated sodium hydrogencarbonate was added. The mixture was extracted with methylene chloride. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to give a solid. This was dissolved in diethyl ether and extracted with 1 N sodium hydroxide which was then acidified to pH 1 and extracted with ethyl acetate. The extract was dried and concentrated to a yellow solid which was recrystalized from ethyl acetate/hexane to give white crystals (1.05 g). MW 231; MS (m/e) 249 (M++NH4+).

Aufarbeitung

  1. extractionThe mixture was extracted with methylene chloride
  2. washThe combined extracts were washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. extractionextracted with 1 N sodium hydroxide which
  8. extractionextracted with ethyl acetate
  9. customThe extract was dried
  10. concentrationconcentrated to a yellow solid which
  11. customwas recrystalized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5c09e90a1c474adaa12a8a64284234f3
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380218B1

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