Potassium Carbonate → 3-[4-(1,1'-Biphenyl-4-ylmethoxy)phenyl]-1-propanol

HRID 1782753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782753
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22](O)[CH2:23][CH3:24])=[CH:18][CH:17]=1.C(=O)([O-])[O-:27].[K+].[K+]>C(#N)CCC>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][C:10]([CH2:11][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][OH:27])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 130555574-(1-Hydroxypropyl)Phenol

Produkt 1

HCID 575890363-[4-(1,1'-Biphenyl-4-ylmethoxy)phenyl]-1-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8008ButyronitrileLösungsmittel

Versuchsvorschrift

12.8 g (41.4 mmol) of 4-phenylbenzyl bromide, 6.94 g (45.6 mmol) of 4-hydroxy-phenylpropanol and 6.87 g (49.7 mmol) of potassium carbonate are stirred in 50 ml of butyronitrile at 120° C. for 6 hours. Cooling to room temperature is followed by removal of the inorganic salts by filtration with suction and concentration in vacuo. The crude product is purified by chromatography on silica gel 60 (mobile phase gradient cyclohexane-->cyclohexane/ethyl acetate 60:40). 4.90 g (37% of theory) of product are obtained.

Aufarbeitung

  1. customis followed by removal of the inorganic salts by filtration with suction and concentration in vacuo
  2. customThe crude product is purified by chromatography on silica gel 60 (mobile phase gradient cyclohexane-->cyclohexane/ethyl acetate 60:40)
  3. custom4.90 g (37% of theory) of product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-93a6c17c3c44457788a844ec68ab49dd
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498460B2

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