Resorcinol → (2-[3-Hydroxyphenoxymethyl]-6-methylphenoxy)acetonitrile

HRID 892154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892154
[C:1]([CH2:3][O:4][C:5]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br)#[N:2].[C:14]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOCC>[OH:15][C:14]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[O:18][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:5]=1[O:4][CH2:3][C:1]#[N:2]

Komponenten

6

Edukt 3

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

Produkt 1

HCID 22241289(2-[3-Hydroxyphenoxymethyl]-6-methylphenoxy)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Heated (60° C.) a mixture of 2-cyanomethoxy-3-methylbenzyl bromide (10.2 g, 42.7 mmoles, example 24), resorcinol (18.8 g, 171 mmoles), and potassium carbonate (47.2 g, 342 mmoles) in acetonitrile (140 mL) for two hours. The reaction is diluted with ether and washed three times with distilled water, once with brine, and dried over MgSO4. The organic layer is isolated and concentrated, and the resulting residue is purified by column chromatography (silica, 5% EtOAc/CH2Cl2) to yield the title compound as a white crystalline solid. MS(EI) 269 (M)+.

Aufarbeitung

  1. washwashed three times with distilled water
  2. dry with materialonce with brine, and dried over MgSO4
  3. customThe organic layer is isolated
  4. concentrationconcentrated
  5. customthe resulting residue is purified by column chromatography (silica, 5% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b9fa7fc851564ba8bade906282d5fb02
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005440B1

Notizen zur Reaktion

Wird geladen…