2,6-Bis(3-pyridyl)phenyl benzyl ether → 2,6-Bis(3-pyridyl)phenol

HRID 2069875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069875
C([O:8][C:9]1[C:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)C1C=CC=CC=1>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:9]=2[OH:8])[CH:16]=1

Komponenten

3

Edukt 1

HCID 581502802,6-Bis(3-pyridyl)phenyl benzyl ether

Produkt 1

HCID 463166362,6-Bis(3-pyridyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2,6-Bis(3-pyridyl)phenyl benzyl ether (16.70 g, 49.35 mmol) was dissolved in MeOH (200 mL). Argon was bubbled through this solution for 10 min to remove oxygen. Then Pd/C (500 mg 5 w %) was added, and the reaction mixture was put into the Parr-reactor and shaken for 16 hr under a hydrogen atmosphere at 80 psi. After the hydrogenation, the resulting precipitate was redissolved by heating to reflux. The hot mixture was filtered over diatomaceous earth, and the filter cake thoroughly washed with hot MeOH. Upon cooling to room temperature, the product crystallized as a white crystalline material (12.25 g, 99%). M.p.=211° C. 1H-NMR (DMSO):δ=8.74 (d, 2H), 8.55 (dd, 2H), 7.95 (dt, 2H), 7.48 (m, 2H), 7.34 (d, 2H), 7.11 (t, 1H).

Aufarbeitung

  1. customArgon was bubbled through this solution for 10 min
  2. customto remove oxygen
  3. additionThen Pd/C (500 mg 5 w %) was added
  4. dissolutionAfter the hydrogenation, the resulting precipitate was redissolved
  5. temperatureby heating to reflux
  6. filtrationThe hot mixture was filtered over diatomaceous earth
  7. washthe filter cake thoroughly washed with hot MeOH
  8. customthe product crystallized as a white crystalline material (12.25 g, 99%)

Quellen und Nachweise

ORD-Eintrag
ord-783196c1fcc94f86baade4a0b860590d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299202B2

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