Water → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 413789

Reaktionsgleichung

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[C:12]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH2:1]([O:19][C:12]1[C:11]([O:10][CH3:9])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Benzyl bromide (8.6 ml) was added to a stirred solution of 3-methoxysalicylaldehyde (10 g), potassium carbonate (14.76 g) and potassium iodide (0.12 g) in DMF (120 ml) under an atmosphere of argon. The reaction was heated at 70° C. for 16 hours. Water (200 ml) was added causing the precipitation of a brown oil which crystallised on cooling. The solid was filtered, washed with water, dissolved in dichloromethane and dried (MgSO4). The solvent was removed in vacuo to give an oil which crystallised on trituration with iso-hexane to give the product as an off white solid (12.85 g, 81%); NMR d (CD3SOCD3) 3.91 (s, 3H), 5.15 (s, 2H), 7.14-7.22 (m, 2H), 7.29-7.42 (m, 6H), 10.10 (t, 1H); M/z (+) 243 (MH+).

Aufarbeitung

customthe precipitation of a brown oil which
customcrystallised
temperatureon cooling
filtrationThe solid was filtered
washwashed with water
dissolutiondissolved in dichloromethane
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customto give an oil which
customcrystallised on trituration with iso-hexane

Quellen und Nachweise

ORD-Eintrag: ord-85cf6ef0ec784178b2581fde72b3ab84
Quelldatensatz: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06569888B1

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