Dimethyl Sulfate → Dimethyl Sulfate

HRID 280721

Reaktionsgleichung

Reaktionsgleichung von HRID 280721
[C:1]1([O:7]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([OH:16])=[O:15].[S:17]([O:22][CH3:23])([O:20][CH3:21])(=[O:19])=[O:18].[C:24](=[O:27])([O-:26])[O-:25].[K+].[K+]>[Na].[OH-].[K+].CC(C)=O>[OH:7][C:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6]=1[C:24]([OH:26])=[O:25].[S:17]([O:22][CH3:23])([O:20][CH3:21])(=[O:19])=[O:18].[CH3:21][O:16][C:14]([C:10]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[O:27][CH3:24])=[O:15]

Komponenten

10

Edukt 4

HCID 6497Dimethyl SulfateHCID 69192-Furancarboxylic acidHCID 7519AnisoleHCID 11430Potassium Carbonate

Produkt 3

HCID 6497Dimethyl SulfateHCID 167902-Hydroxy-1-naphthoic acidHCID 604022Methyl 2-methoxy-1-naphthoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 14797Potassium HydroxideLösungsmittelHCID 5360545SodiumLösungsmittel

Versuchsvorschrift

This methyl ester was previously made by fusion of anisole and 2-furoic acid followed by esterification of the acid intermediate, J. Amer. Chem. Soc., Vol. 69, 2261 (1947). Methyl esters of methoxy carboxylic acids were prepared by methylation of aromatic hydroxy carboxylic acids with dimethyl sulfate in the presence of potassium carbonate as base, using acetone as the solvent, Houben-Weyl, Methoden der Organischen Chemie., Vol. 8, 542-3 (1952). Methylation of 2-hydroxy-1-naphthoic acid with dimethyl sulfate in aqueous sodium or potassium hydroxide produced mainly methyl-2-methoxy-1-naphthalenecarboxylate, Chemische Berichte, Vol. 37, 3658-61 (1904). In aqueous solutions, at pH 4-6.5, methylation of hydroxy napthoic acids with dimethyl sulfate produced the methyl esters of the hydroxy naphthoic acids.

Quellen und Nachweise

ORD-Eintrag
ord-c324ab068a684be1923eb42b45f5f752
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590290

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