Water → 4'-Methoxymethoxy-1,1'-biphenyl-4-carbonitrile

HRID 2076697

Reaktionsgleichung

Reaktionsgleichung von HRID 2076697
[CH3:1][O:2][CH2:3]Cl.C(N(C(C)C)CC)(C)C.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.O>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Produkt 1

HCID 601021314'-Methoxymethoxy-1,1'-biphenyl-4-carbonitrileAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Chloromethyl methyl ether (0.5 ml, 6.59 mmol) and diisopropylethylamine (1.44 ml, 8.24 mmol) were added to a solution of 4′-hydroxy-1,1′-biphenyl-4-carbonitrile (1.07 g, 5.49 mmol) in methylene chloride (10 ml), and the mixture was stirred at room temperature for 16 hours. After water was added to the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1) to give 4′-methoxymethoxy-1,1′-biphenyl-4-carbonitrile (1.03 g, yield: 78%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous NaCl solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-71523a5ac47d47f6b7434d0d009eb619
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923573B2

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