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Green synthesis method of acetal-type or ketal-type compound

A synthesis method and compound technology, applied in the field of preparation of organic compounds, can solve the problems of narrow substrate range, difficulty in preparation, and expensive raw materials, and achieve the effects of simple preparation, recovery, and reduced reaction conditions

Inactive Publication Date: 2016-08-17
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the reaction temperature is -20°C, and the catalyst is expensive and difficult to prepare. These problems make it difficult to realize the reaction system in industrial production.
The disadvantage is that the substrate range of this system is narrow, the yield of dihydric alcohol is low, and the catalyst synthesis method is complicated and the raw material is expensive
[0017] In 2013, Connon et al. [9] It is reported that tetrafluoroborate of triazole derivatives is used as a catalyst to prepare acetal compounds from aldehyde compounds under the action of 1 mol% catalyst, and the reaction yield is high, but the ketalization reaction of ketones is not reported. There is also no indication of the scope of application of alcohols as substrates
[0018] In 2013, Gathergood et al. [10] reported the use of 3,4-dicarboxylate imidazolium tetrafluoroborate as a small organic molecule catalyst, methanol as a reactant and solvent, to achieve efficient conversion of aldehydes and ketones in the carbonyl alcohol condensation, but the catalyst exists diols Problems such as low yield and narrow substrate range

Method used

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  • Green synthesis method of acetal-type or ketal-type compound
  • Green synthesis method of acetal-type or ketal-type compound
  • Green synthesis method of acetal-type or ketal-type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The reaction formula is as follows:

[0053]

[0054] Concrete reaction process is as follows:

[0055] Add benzaldehyde (0.2mol, 21.2g) successively in a four-necked flask equipped with stirrer and thermometer, hydrogen-carrying catalyst AcrH 2 0.26g, 100mL of methanol, stirred and reacted at room temperature for 24h; after the reaction was completed, excess methanol was recovered by distillation, and 26.7g of light yellow liquid benzaldehyde dimethyl acetal was obtained by distillation under reduced pressure, with a yield of 88%.

[0056] Product NMR data: 1 H NMR (600MHz, CDCl 3 )δ7.46(s, 2H), 7.37(d, J=7.1Hz, 2H), 7.32(t, J=7.2Hz, 1H), 5.39(s, 1H), 3.33(s, 6H); 13 C NMR (151MHz, CDCl 3 )δ137.99(s), 128.41(s), 128.16(s), 126.64(s), 103.11(s), 52.67(s).

Embodiment 2

[0058] The reaction formula is as follows:

[0059]

[0060] Concrete reaction process is as follows:

[0061] In a four-necked flask equipped with stirrer and thermometer, add phenylacetaldehyde (0.2mol, 24g) successively, hydrogen-carrying catalyst AcrH 2 0.26g, methanol 100mL, stirred and reacted at room temperature for 24h; after the reaction, first distilled to recover excess methanol, and distilled under reduced pressure to obtain 27.2g of light yellow liquid phenylacetaldehyde dimethyl acetal with elegant fragrance, yield 82% .

[0062] Product NMR data: 1 H NMR (600MHz, CDCl 3 )δ7.30(d, J=7.6Hz, 2H), 7.24(s, 2H), 7.21(d, J=7.2Hz, 1H), 4.54(t, J=5.6Hz, 1H), 3.34(s, 6H), 2.91(s, 2H); 13 C NMR (151MHz, CDCl 3 )δ137.03(s), 129.40(s), 128.29(s), 126.34(s), 105.34(s), 53.31(s), 39.67(s).

Embodiment 3

[0064] The reaction formula is as follows:

[0065]

[0066] Concrete reaction process is as follows:

[0067] Add phenylpropanal (0.2mol, 26.8g) successively in a four-necked flask equipped with stirrer and thermometer, hydrogen-carrying catalyst AcrH 2 0.26g, 100mL of ethanol, stirred and reacted at room temperature for 24h; after the reaction, the excess ethanol was recovered by distillation first, and then distilled under reduced pressure to obtain 26.7g of colorless liquid phenylpropionaldehyde diethyl acetal with a light and elegant fragrance, with a yield of 64% .

[0068] Product NMR data: 1 H NMR (600MHz, CDCl 3 )δ7.30–7.27(m,2H,ArH),7.22(d,J=7.6Hz,2H,ArH),7.20(d,J=7.3Hz,1H,ArH),4.51(t,J=5.7Hz ,1H,CH),3.68(dq,J=14.2,7.1Hz,2H,CH 2 ), 3.52 (dq, J=14.3, 7.1Hz, 2H, CH 2 ),2.74–2.68(m,2H,CH 2 ),2.00–1.94(m,2H,CH 2 ), 1.24(t, J=7.1Hz, 6H, CH 3 ); 13 C NMR (151MHz, CDCl 3 )δ141.78(s), 128.39(s), 128.34(s), 125.78(s), 102.19(s), 61.02(s), 35.09(s), 31.01(s), 15...

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Abstract

The invention discloses a green synthesis method of an acetal-type or ketal-type compound. A carbonyl compound is used as a raw material, a hydrogen-loaded compound is used as a catalyst, then an alcohol substance is added, a reaction is performed to generate the acetal-type or ketal-type compound. The synthesis method is simple and convenient, is high in conversion rate and yield, is safe and stable, has low toxicity and is easy to operate; the used catalyst is simple to prepare, and is cheap and easy to obtain; the reaction process is mild and efficient; the product is easy to separate and purify; the green synthesis method has a wide substrate application range, can be used for synthesizing acetal and ketal spices, and has potential industrial application value.

Description

1. Technical field [0001] The invention relates to a preparation method of organic compounds, in particular to a green synthesis method of acetal or ketal compounds. 2. Background technology [0002] The carbonylation reaction of aldehydes or ketones is a very important class of organic reactions, and is often used for the protection of carbonyl groups in multi-step synthesis. Carbonyl compounds are not only important pharmaceutical intermediates, but also important chemical products used in industries such as food additives, spices, surfactants and polymer materials. Traditionally, the methods for synthesizing acetal and ketal compounds mostly use inorganic acids such as HCl, H 2 SO 4 , BF 3 .Et 2 Catalytic methods such as O and TFA have low reaction yields and large amounts of catalysts, and the use of inorganic acids also has the disadvantages of polluting and corroding equipment. Studies in recent years have found that solid superacids, metal salts, ionic solutions ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/04C07C43/307C07C43/303C07C43/305C07C41/56C07C205/34C07C201/12C07D339/06C07D317/22
CPCC07B41/04C07C41/56C07C201/12C07D317/22C07D339/06C07C43/307C07C43/303C07C43/305C07C205/34
Inventor 冯乙巳刘亮亮程志非徐卓玮
Owner HEFEI UNIV OF TECH