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Preparation method of 1,2,3-cyclopropyl tricarboxylate

A technology of cyclopropanetricarboxylic acid and triethyl ester, which is applied in the field 1, can solve problems such as difficult preparation, high price, and environmental pollution, and achieve the effect of low cost and low cost

Inactive Publication Date: 2010-09-29
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For the first method, 5,15-bis[2,6-bis[[[((1S)-2,2-dimethylcyclopropyl)carbonyl]amino]phenyl]-10,20- Bis(3,5-di-tert-butylphenyl)porphate]cobalt (CAS: 811435-11-7) as a catalyst is difficult to prepare and expensive, so it is not suitable for industrial production of 1,2,3 -Triethyl cyclopropanetricarboxylate; For the second method, raw material S, ethyl dimethyl acetate is difficult to prepare, and the reaction will produce dimethyl sulfide, which will pollute the environment; For the third method, it is necessary to use Dichlorotri-(triphenylphosphine)ruthenium (CAS: 15529-49-4) is expensive as a catalyst, and when using this process, the yield of 1,2,3-cyclopropanetricarboxylic acid triethyl only 10%

Method used

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  • Preparation method of 1,2,3-cyclopropyl tricarboxylate
  • Preparation method of 1,2,3-cyclopropyl tricarboxylate

Examples

Experimental program
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Embodiment 1

[0016] Embodiment 1, a kind of preparation method of 1,2,3-triethyl cyclopropanetricarboxylate, carries out following steps successively:

[0017] Step 1), prepare ethyl diazoacetate:

[0018] Put 14.0g (0.1mol) glycine ethyl ester hydrochloride, 20ml water, 1ml mass concentration 98% concentrated sulfuric acid, and 50ml dichloroethane into a 250ml flask, cool to 10°C, and add 25ml nitrous acid dropwise under stirring Aqueous sodium solution (27.5%, 0.11 mol), dripped over 20 minutes, and stopped the reaction after stirring for 30 minutes. Separation, the aqueous phase was extracted with dichloroethane (2 × 20ml), the combined organic phase was washed with saturated sodium bicarbonate solution (2 × 10ml), dried over anhydrous magnesium sulfate (refer to "Fine Chemical Intermediates" 2008, 38 (1): 40~43), obtain the dichloroethane solution 118.0g of ethyl diazoacetate (GC analysis ethyl diazoacetate content is 9.1%, equivalent to pure ethyl diazoacetate 10.7g), the weight of g...

Embodiment 2～8

[0022] Step 1) is the same as in Example 1.

[0023] Change the following reaction conditions in the step 2) of embodiment 1:

[0024] Step 2) in organic solvent (being called for short S), the quality of organic solvent and ethyl diazoacetate mass ratio (being called for short R in step 2) 1 ), catalyst (abbreviated as C) in step 2, the quality of catalyst in step 2 and ethyl diazoacetate mass ratio (abbreviated as R 2 ), temperature of reaction (abbreviated T) in step 2, reaction time (abbreviated t) in step 2, dripping ethyl diazoacetate time (abbreviated t) in step 2 1 ), continue the reaction time in step 2 (referred to as t 2 ), t=t 1 +t 2 , to obtain Examples 2-8, thereby obtaining the corresponding yield of 1,2,3-triethyl cyclopropanetricarboxylate (abbreviated as Y). See Table 1 for details and data results.

[0025] Table 1

[0026] Example

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Abstract

The invention discloses a preparation method of 1,2,3-cyclopropyl tricarboxylate, comprising the following steps of: heating ethyl diazoacetate as a raw material for carrying out a cyclization reaction in the presence of organic solvents and catalysts at the reaction temperature of 35-110DEG C for 2-6h, wherein the mass ratio of the catalysts to the ethyl diazoacetate is 1:10-50; and rectifying after the reaction is finished to obtain the 1,2,3-cyclopropyl tricarboxylate. The method for preparing the 1,2,3-cyclopropyl tricarboxylate has the characteristics of concise process, high yield, low cost and less discharge of three wastes.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 1,2,3-cyclopropanetricarboxylic acid triethyl ester. Background technique [0002] 1,2,3-Triethyl cyclopropanetricarboxylate, whose molecular formula is C 12 h 18 o 6 , whose structural formula is shown in S-1; soluble in cyclohexane, dichloromethane, dichloroethane, etc., almost insoluble in cold water, is an important fine chemical intermediate, mainly used for the synthesis of 1, 2, 3 - Trimethylenecyclopropane (CAS: 66767-55-3), cyclopropane-1,2,3-triamine (CAS: 5794-73-0) and other products. [0003] [0004] Comprehensive literature report, at present 1,2, the preparation of 3-cyclopropanetricarboxylate triethyl ester mainly adopts following several methods: 1, adopt diethyl crotonate and ethyl diazoacetate to react under the effect of catalyst Generate 1,2,3-cyclopropanetricarboxylic acid triethyl ester, the reaction formula is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/74C07C67/343C07C67/313C07C67/317
Inventor 陈新志张华钱超
Owner ZHEJIANG UNIV
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