Diethyl Carbonate → Diethyl 2-(m-phenoxyphenyl)malonate

HRID 1732441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1732441
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23].[Na]>>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([C:20]([O:21][CH2:22][CH3:23])=[O:24])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 12509092Ethyl (3-phenoxyphenyl)acetate

Produkt 1

HCID 11472917Diethyl 2-(m-phenoxyphenyl)malonate

Versuchsvorschrift

The method which comprises brominating m-methyldiphenyl ether with N-bromosuccinimide to form m-(bromomethyl)diphenyl ether, reacting it with sodium cyanide in dimethylsulfoxide to form m-(cyanomethyl)diphenyl ether, hydrolyzing and esterifying it to form ethyl α-(m-phenoxyphenyl)acetate, reacting the resulting ester with diethyl carbonate in the presence of metallic sodium to form diethyl 2-(m-phenoxyphenyl)malonate, reacting the product with methyl iodide to form diethyl 2-methyl-2-(m-phenoxyphenyl)-malonate, hydrolyzing the product to form 2-methyl-2-(m-phenoxyphenyl)malonic acid, and decarboxylating the product under heat to form α-(m-phenoxyphenyl)propionic acid (Japanese Pat. No. 45586/76).

Quellen und Nachweise

ORD-Eintrag
ord-5bd7fa39e73742adaa88cb02e3fec90b
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04237298

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