Orcinol → 3-[2-(4-Cyanophenyl)ethoxy]-5-methylphenol

HRID 325049

Reaktionsgleichung

Reaktionsgleichung von HRID 325049
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([OH:27])[CH:26]=1.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38]O)=[CH:33][CH:32]=1)#[N:30].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][O:20][C:21]2[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([CH3:28])[CH:22]=2)=[CH:33][CH:32]=1)#[N:30]

Komponenten

6

Edukt 4

HCID 10436OrcinolHCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 220335303-[2-(4-Cyanophenyl)ethoxy]-5-methylphenolAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphoshine (7.86 g; 30 mmol), 3,5-dihydroxytoluene (2.5 g; 20 mmol) and 2-(4-cyanophenyl)ethanol (4.41 g; 30 mmol) were dissolved in THF (50 mL). Diethylazodicarboxylate (5.22 g; 30 mmol; dissolved in THF (10 mL)), was added and the solution was stirred at room temperature overnight. The solvent was removed in vacuo and the white solid residue extracted with Et2O. Purification by flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 1.85 g (37%) of the sub-title compound as a white solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionthe white solid residue extracted with Et2O
  3. customPurification by flash chromatography (SiO2; toluene:EtOAc (10:1))

Quellen und Nachweise

ORD-Eintrag
ord-c75018db129c4a1882a1a70317255148
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221898B1

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