Dimethyl Sulfate → Dimethyl Sulfate

HRID 280721

Reaction equation

HRID 280721 reaction equation
[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]

Participants

10

Reactant 4

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

Product 3

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 14797Potassium HydroxideSolventHCID 5360545SodiumSolvent

Procedure

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.

Sources & evidence

ORD record
ord-c324ab068a684be1923eb42b45f5f752
Source dataset
uspto-grants-1986_05
Patent number
US04590290

Linked notes

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