2-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanol → 2-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol

HRID 1455021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455021
C([O:8][C:9]1[CH:24]=[CH:23][C:22]([O:25]CC2C=CC=CC=2)=[CH:21][C:10]=1[O:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])C1C=CC=CC=1>C(O)C.[Pd]>[OH:14][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][O:11][C:10]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:9]=1[OH:8]

Komponenten

4

Edukt 1

HCID 179784692-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanol

Produkt 1

HCID 179786042-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-[2,5-bis(benzyloxy)phenoxy]-1-phenylethanol (3.9 g) in ethanol (175 ml) was hydrogenated in the presence of 10% palladium on charcoal (100 mg) at 30 psi. The catalyst was removed by filtration and the solvent was evaporated under reduced pressure. The residue was recrystallized from the mixture of toluene-ethyl acetate 8:1 (15 ml). The yield of 2-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol is 1.2 g. 1H NMR (DMSO-d6) δ: 3.79 (dd, J 9.6, 8.3 Hz, 1H), 4.00 (dd, J 9.6, 3.6 Hz, 1H), 4.94 (ddd, J 3.6, 8.3, 3.9 Hz, 1H), 5.66 (d, J 3.9 Hz, 1H), 6.18 (dd, J 8.5, 2.3 Hz, 1H), 6.34 (d, J 2.3, 1H), 6.57 (d, J 8.5, 1H), 7.26-7.47 (m, 5H), 7.97 (s, 1H), 8.66 (s, 1H).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was recrystallized from the mixture of toluene-ethyl acetate 8:1 (15 ml)

Quellen und Nachweise

ORD-Eintrag
ord-78f143813fbb4171857fad7b5ed8bf5c
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482340B2

Notizen zur Reaktion

Wird geladen…