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Production of 4,4-dimethyl-3-ketone-methoxycarbonyl valerate

A technology of methyl valerate and methyl pivalate, applied in the field of chemical engineering, to achieve the effects of low volatilization loss, easy recovery, and reduced energy consumption

Inactive Publication Date: 2007-11-21
KAILONGHUA CHEM HANGZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of using acylated ester and acetate to synthesize β-ketoester has been reported in a patent registered in 2006, but the solvent used is DMSO, and the yield of reaction is only 53% (Deinhammer claims W., Germany Patent No. 102004047713 (2006))

Method used

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  • Production of 4,4-dimethyl-3-ketone-methoxycarbonyl valerate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Weigh 4.6 grams (0.04 moles) of anhydrous methyl pivalate, 1.6 grams of 60% pure sodium hydride (0.04 moles) dispersed in mineral oil and 20 milliliters of dry toluene, mix and stir under nitrogen protection to form a suspension, At the same time, the temperature was raised to 60-65° C., and then a total of 3 g of dry methyl acetate (0.04 mol) was added dropwise. After the addition was completed within about 0.5 hours, the stirring reaction was continued for 1 hour. Cool to room temperature with stirring. Add 4-5 grams of crushed ice to the reaction solution, then add about 7 ml of 5 mol / L hydrochloric acid to pH 4-5, stir and separate layers, remove the lower aqueous phase, and wash twice with 10 ml of clean water until neutral. The organic phase was dehydrated and filtered with anhydrous sodium sulfate, and the toluene was recovered by distillation; after the solvent was removed, the product 1,4-dimethyl-3-keto-methyl valerate was extracted by distillation under reduc...

Embodiment 2

[0030] Under nitrogen protection, 23.2 grams (0.2 moles) of anhydrous methyl pivalate were dissolved in 100 milliliters of dry toluene, and then 8 grams of sodium hydride (0.2 moles) of 60% purity dispersed in mineral oil were added at one time, and stirred The temperature was raised to 65-70°C, and then a total of 14.8 g of dry methyl acetate (0.2 mol) was slowly added dropwise, and the addition was completed within about 1 hour, and the reaction was continued to stir for 1 hour. Cool to room temperature with stirring. Add 20 grams of crushed ice to the reaction liquid, then add about 42 ml of 5 mol / L hydrochloric acid to pH 4-5, stir and separate layers, remove the lower aqueous phase, and wash twice with 50 ml of clean water until neutral. The organic phase was dehydrated and filtered with anhydrous sodium sulfate, and the toluene was recovered by distillation; after the solvent was removed, the product 1,4-dimethyl-3-keto-methyl valerate was extracted by distillation under...

Embodiment 3

[0032] Weigh 80 grams of 60% sodium hydride (2 moles) and add it into a reaction flask with nitrogen gas, then add 1000 milliliters of dry toluene and 232 grams (2 moles) of anhydrous methyl pivalate at one time, and heat up to 60- 65°C, and then slowly add a total of 148 g of dry methyl acetate (2 moles) dropwise, and the addition is completed within about 2 hours, and the reaction is continued for 2 hours with stirring. Cool to room temperature with stirring. Add 200 grams of crushed ice to the reaction liquid, then add about 420 ml of 5mol / L hydrochloric acid to pH 4-5, stir and then separate into layers, remove the lower aqueous phase, and wash twice with 500 ml of clean water until neutral. The organic phase was dehydrated and filtered with anhydrous sodium sulfate, and the toluene was recovered by distillation; after the solvent was removed, the product 1,4-dimethyl-3-keto-methyl valerate was extracted by distillation under reduced pressure to obtain 290 grams of 1 with ...

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Abstract

Production of 4,4-methyl-3-ketone-pentoic acid carbomethoxy is carried out by anhydrous tementhyl valerate and dried acetate carbomethoxy as raw materials, taking sodium hydride as catalyst, taking toluene as solvent, agitating while reacting at 60-70 degree, cooling, regulating pH value to 4-5, laying aside, stratifying, removing solvent, decompressing, distilling and extracting to obtain final product. It costs low and has more yield.

Description

technical field [0001] The invention relates to the field of chemical engineering, in particular to a method for preparing 4,4-dimethyl-3-keto-methyl valerate from methyl pivalate and methyl acetate. Background technique [0002] 4,4-Dimethyl-3-keto-valeric acid methyl ester is a key intermediate widely used in the preparation of photosensitive materials. There have been many patent reports on its synthetic method since 1994. The preparation of methyl 4,4-dimethyl-3-keto-pentanoate by the condensation reaction of pinacolone and dimethyl carbonate under different reaction conditions is described. Compared with general carboxylic acid esters, dimethyl carbonate is not easy to react, and relatively strong reaction conditions need to be adopted. As far as industrial applications are concerned, these methods have some defects that need to be improved in terms of cost, ease of operation and product purity control. Specifically, the method (Boaz, N.W. et al., U.S. Patent No. 9,8...

Claims

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Application Information

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IPC IPC(8): C07C69/716C07C67/313
Inventor 王光迪金志豪
Owner KAILONGHUA CHEM HANGZHOU
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