4-Aminophenol → tert-Butyl 3-amino-4-hydroxybenzoate

HRID 25263

Reaktionsgleichung

Reaktionsgleichung von HRID 25263
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([O:16]C(OC(C)(C)C)=O)=O)([CH3:12])([CH3:11])[CH3:10].C([N:27](C(C)C)CC)(C)C>C1COCC1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([NH2:27])[CH:3]=1)([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:16]

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 11160103tert-Butyl 3-amino-4-hydroxybenzoateAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-aminophenol (10.9 g, 100 mmol) in THF (150 mL) cooled in an ice bath was added di-tert-butyl-dicarbonate (21.8 g, 100 mmol) followed by diisopropylethylamine (17.4 mL, 100 mmol). The mixture was stirred at room temperature overnight and concentrated. The residue was taken up in ethyl acetate and the solution was washed with brine, dried (MgSO4), and concentrated. Purification on a silica gel column eluting with 5% methanol/40% ethyl acetate hexane gave 4Boc-aminophenol (20.1 g, 96%). MS(NH3—CI): (M+NH3+H)=227.

Aufarbeitung

  1. concentrationconcentrated
  2. washthe solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on a silica gel column
  6. washeluting with 5% methanol/40% ethyl acetate hexane

Quellen und Nachweise

ORD-Eintrag
ord-a263a6c6aab24b52ae051db78b79b634
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858626B2

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