tert-Butanol → HCID 22010963, Verbindung

HRID 323135

Reaktionsgleichung

Reaktionsgleichung von HRID 323135
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[NH:38][C:41]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 224521542-(Benzyloxy)-4-chlorobenzoic acid

Produkt 1

HCID 22010963HCID 22010963, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

2-Benzyloxy-4-chlorobenzoic acid (3.0 g) was heated under reflux in a mixture of benzene and t-butyl alcohol. Diphenylphosphoryl azide (3.14 g) and triethylamine (1.21 g) were added in one batch to the mixture and reflux was continued for a further 8 hours. Benzene was removed under reduced pressure and the residue taken up in ethyl acetate. An insoluble white solid was removed by filtration. The remaining organic filtrate was washed successively with diluted hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated to give 2-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline (1.6 g).

Aufarbeitung

  1. temperaturereflux
  2. customBenzene was removed under reduced pressure
  3. customAn insoluble white solid was removed by filtration
  4. washThe remaining organic filtrate was washed successively with diluted hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2e09c12c1f6b4a26b67542010047bcc9
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211242B1

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