4-Aminophenol → 6-[(4-Hydroxyphenyl)amino]-2-naphthalenol

HRID 1165491

Reaktionsgleichung

Reaktionsgleichung von HRID 1165491
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15](O)[CH:16]=2)[CH:11]=1.S(=O)(O)[O-].[Na+]>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([OH:9])[CH:19]=[CH:18]3)=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 935522,6-DihydroxynaphthaleneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 144992086-[(4-Hydroxyphenyl)amino]-2-naphthalenolAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 300 mg (2.75 mmol, Aldrich) of 4-aminophenol, 1.5 g (90%, 8.4 mmol, Aldrich) of 2,6-dihydroxynaphthalene and 1.0 g (9.6 mmol, Aldrich) of sodium bisulfite in 30 ml of H2O was refluxed for 18 hours. The reaction mixture was cooled, added to 30 ml of H2O and extracted with two 25 ml portions of ethyl aetate. The organic extracts were combined, dried (MgSO4), and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether) followed by recrystallization (EtOAc/pet ether) to afford 215 mg (31%) of title compound as pale pink crystals, m.p. 195°-196°.

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with two 25 ml portions of ethyl aetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThe crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether)
  8. customfollowed by recrystallization (EtOAc/pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-041918367abf4f3d915d18069f98fa52
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910208

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