Water → (E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate

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Reaktionsgleichung

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].P([O-])([O-])(O)=[O:18].[Na+].[Na+].P([O-])([O-])(O)=O.[K+].[K+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:18]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of (E)-methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (10.0 g, 90% pure), sodium hydrogen orthophosphate dibasic (Na2HPO4, 5.74 g) and potassium hydrogen monophosphate monobasic (KH2PO4, 0.55 g) in DMSO (20 ml) was heated at 80° C. for 1 hour and then at 110° C. for a further hour (compare J. H. Babler, M. J. Coghlan, M. Feng and P. Fries, J. Org. Chem., 1979, 44, 1716). After cooling, the reaction mixture was poured into water and extracted with ether. The extracts were washed with brine, dried, concentrated and chromatographed using ether as eluant to give (E) -methyl 2-(2-formylphenyl)-3-methoxypropenoate (2.77 g, 40% yield) as a white crystalline solid, m.p. 67°-69° C. IR (nujol): 1710, 1634 cm-1. 1H NMR: delta 3.72 (3H, s), 3.84 (3H, s), 7.30-7.65 (3H, m), 7.69 (1H, s), 7.9 (1H, m), 10.0 (1H, s) ppm.

Aufarbeitung

waitat 110° C. for a further hour (compare J. H. Babler, M. J. Coghlan, M. Feng and P. Fries, J. Org. Chem., 1979, 44, 1716)
temperatureAfter cooling
extractionextracted with ether
washThe extracts were washed with brine
customdried
concentrationconcentrated
customchromatographed

Quellen und Nachweise

ORD-Eintrag: ord-c6f00cc89feb481aa2812793272c265f
Quelldatensatz: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05438059

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