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US 4,065,504 AGranted
Process for the methylation of hydroxybenzene derivatives
AssigneeDomtar Inc.
InventorDavid Michael Findlay
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Abstract
A method is disclosed of alkylating substituted hydroxybenzenes, particularly substituted hydroxybenzaldehydes, by reacting the hydroxybenzene compound with a dialkylsulfate in the presence of an alkali metal carbonate, substantially in the absence of a solvent. The alkoxylated product is obtained in yields substantially close to theoretical.
Claims10
A method of preparing a carbonyl-substituted alkoxybenzene comprising
- a. forming a mixture consisting essentially of a carbonyl-substituted hydroxybenzene, a dialkyl sulfate and sodium carbonate, said carbonyl-substituted hydroxybenzene being one of the class consisting of hydroxybenzaldehyde, di-hydroxybenzaldehyde, vanillin, hydroxyvanillin, syringealdehyde, hydroxyveratraldehyde, acetovanillone and aceto-syringeone, and said dialkyl sulphate being one of the group consisting of dimethyl sulfate and diethyl sulfate, the molar ratios of said dialkyl sulfate and of said sodium carbonate to said hydroxybenzine being, respectively, between 1.1 and 2 to 1 and between 1 and 2 to 1,
- b. heating said mixture to a fluidizing temperature at which said carbonyl-substituted hydroxybenzene and said dialkyl sulfate form a substantially homogeneous liquid medium and said sodium carbonate is suspended in said medium,
- c. maintaining said mixture at a temperature at least equal to said fluidizing temperature,
- d. stirring said mixture thereby to promote an alkylation reaction in said mixture and produce a carbonyl substituted alkoxybenzene from said hydroxybenzene, and
- e. adding lubricating water to said mixture during said alkylation reaction in amount just sufficient to maintain said mixture stirrable during said reaction.
2 more elements
A process for the preparation of 3,4,5-trimethoxybenzaldehyde, comprising:
- a. forming a mixture consisting essentially of a substituted hydroxybenzaldehyde of the group consisting of syringealdehyde, 5-hydroxyveratradehyde and 5-hydroxyvanillin with dimethyl sulfate and sodium carbonate, the molar ratios of said dimethyl sulfate and of said sodium carbonate to said hydroxybenzene being, respectively, between 1.2 and 2 to 1 and between 1 and 2 to 1;
- b. heating said mixture to a fluidizing temperature at which said substituted hydroxybenzaldehyde and dimethyl sulfate form a substantially homogeneous liquid mexium and said carbonate is suspended in said medium, and
- c. maintaining said mixture at a temperature at least equal to said fluidizing temperature,
- d. stirring said mixture thereby to promote a methylation reaction in said mixture and produce a substituted methoxybenzaldehyde from said hydroxybenzaldehyde;
- and
- e. adding lubricating water to said mixture during said methylation reaction in an amount just sufficient to maintain said mixture stirrable during said reaction.
3 more elements
Dependencies are inferred from the claim text.