Potassium Carbonate → Methyl 2-(formyl-5-methylphenoxy)propionate

HRID 257349

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[CH:8][CH:9]=1)[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>CC(=O)CC>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=1[O:10][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 6.0 g (0.0441 mole) of 4-methylsalicylaldehyde, 7.31 g (0.0529 mole) of potassium carbonate, and 8.62 g (0.0529 mole) of methyl 2-bromopropionate in 50 mL of 2-butanone was heated at 70° C. for approximately seventeen hours. The mixture was then filtered, and the filtrate was evaporated under reduced pressure, leaving a light yellow oil as a residue. This oil was placed on a silica gel column and eluted first with diethyl ether/petroleum ether (25/75) and then with diethyl ether. After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 8.2 g of methyl 2-(2-formyl-5-methylphenoxy)propionate was recovered as a white solid, m.p. 65°-68° C. The NMR and IR spectra were consistent with the proposed structure.

Aufarbeitung

filtrationThe mixture was then filtered
customthe filtrate was evaporated under reduced pressure
customleaving a light yellow oil as a residue
washeluted first with diethyl ether/petroleum ether (25/75)
customthe solvents evaporated under reduced pressure, 8.2 g of methyl 2-(2-formyl-5-methylphenoxy)propionate
customwas recovered as a white solid, m.p. 65°-68° C

Quellen und Nachweise

ORD-Eintrag: ord-21867b433e8a4999b87a1adbc6af0b7c
Quelldatensatz: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05262390

Verknüpfte Notizen

Wird geladen…