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Novel synthesis method of ester compound

A technology for ester compounds and a synthesis method, which is applied in the field of ester compound synthesis, can solve the problems of narrow substrate range and low reaction yield, and achieves the effects of environmental friendliness, simple reaction operation and high atom utilization rate.

Pending Publication Date: 2020-05-22
NORTHWEST UNIV(CN) +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In these literatures, the substrate range is narrow (the former only uses methyl vinyl ketone, the latter only acetic acid), and more expensive reagents [eg, PdCl 2 (MeCN) 2 , proline (0.5 equivalent)], and the reaction yield is generally low

Method used

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  • Novel synthesis method of ester compound
  • Novel synthesis method of ester compound
  • Novel synthesis method of ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Add Na to a 10 mL single-necked small flask 2 CO 3 Aqueous solution (0.2 M, 0.5 mL), then added phenyl vinyl ketone (132 mg, 1.0 mmol) and acetic acid (120 mg, 2.0 mmol) in sequence, stirred and reacted at room temperature for 12 h, detected the reaction by TLC plate, and the reaction of raw materials was complete . Then add 30 ml of ethyl acetate, wash with water successively, wash with saturated brine, wash with anhydrous Na 2 SO 4 It was dried, filtered, concentrated under reduced pressure, and separated by column chromatography to obtain compound 1 (175 mg, 91%).

[0022] White solid, melting point 54-55 o C; 1 H NMR (400 MHz, CDCl 3 ): δ 7.96 (d, J = 7.6 Hz,2H), 7.57 (d, J = 7.2 Hz, 1H), 7.48 (t, J = 7.6 Hz, 2H), 4.52 (t, J = 6.3 Hz,2H), 3.32 (t, J = 6.3 Hz, 2H), 2.03 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ196.97, 170.97, 136.52, 133.39, 128.66, 128.02, 59.61, 37.28, 20.86.

Embodiment 2

[0024]

[0025] Add Na to a 10 mL single-necked small flask 2 CO 3 Aqueous solution (0.2 M, 0.5 mL), then add phenyl vinyl ketone (132 mg, 1.0 mmol) and benzoic acid (244 mg, 2.0 mmol) successively, stir the reaction at room temperature for 12 h, TLC plate detection reaction, raw material reaction completely. Then add 30 ml of ethyl acetate, wash with water successively, wash with saturated brine, wash with anhydrous Na 2 SO 4 It was dried, filtered, concentrated under reduced pressure, and separated by column chromatography to obtain compound 2 (163 mg, 64%).

[0026] White solid; melting point 55-56 o C; 1 H NMR (400 MHz, CDCl 3 ): δ 7.99 (d, J = 8.2Hz, 4H), 7.65 – 7.36 (m, 6H), 4.78 (t, J = 6.4 Hz, 2H), 3.45 (t, J = 6.4 Hz,2H); 13 C NMR (100 MHz, CDCl 3 ): δ197.12, 166.57, 136.66, 133.47, 133.04, 130.06, 129.65, 128.76, 128.37, 128.16, 60.35, 37.57.

Embodiment 3

[0028]

[0029] Add Na to a 10 mL single-necked small flask 2 CO 3 Aqueous solution (0.2 M, 0.5 mL), then add phenyl vinyl ketone (132 mg, 1.0 mmol) and cinnamic acid (296 mg, 2.0 mmol) successively, stir the reaction at room temperature for 12 h, TLC plate detection reaction, raw material reaction completely. Then add 30 ml of ethyl acetate, wash with water successively, wash with saturated brine, wash with anhydrous Na 2 SO 4 It was dried, filtered, concentrated under reduced pressure, and separated by column chromatography to obtain compound 3 (202 mg, 72%).

[0030] White solid, melting point 70-71 ºC; IR (KBr, cm -1 ) υ 3401, 2977, 1709, 1633, 1337, 1182, 996, 747, 688, 487; 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (d, J = 8.0 Hz, 2H), 7.66 (d, J = 16.0 Hz, 1H), 7.56 (d, J = 4.0 Hz, 1H), 7.48 (d, J= 8.0 Hz,4H), 7.36 (s, 3H), 6.41 (d, J = 16.0 Hz, 1H), 4.66 (t, J = 6.0 Hz, 2H), 3.39(t, J = 6.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 197.06, 166.82, 145.03,...

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Abstract

The invention discloses a synthesis method of an ester compound. The method comprises the following steps: carrying out an oxa-Michael addition reaction by using organic carboxylic acid and alpha,beta-unsaturated ketone as initial raw materials and a sodium carbonate aqueous solution as a reaction medium to synthesize the ester compound. Compared with the traditional ester compound synthesis method, the method provided by the invention has the advantages of mild reaction conditions, simple operation, low reagent price, wide substrate application range, environmental friendliness, high yield and complete atom utilization.

Description

technical field [0001] The invention relates to a new method for synthesizing ester compounds, which belongs to the field of organic synthesis. Background technique [0002] Esters are a very important class of organic compounds, which widely exist in nature, such as ethyl acetate in wine and vinegar, isoamyl acetate in bananas and pears, isoamyl valerate in apples, and isoamyl acetate in jasmine. Methyl benzoate. Esters are inseparable from floral, fruity, wine and honey aromas, so esters play a particularly important role in fragrances. Low-molecular-weight esters can also be used as solvents and basic chemical raw materials, and are used in many chemical industries. For example, methyl methacrylate is a monomer for the manufacture of plexiglass (polymethyl methacrylate). Larger molecular weight esters, such as polyester resins, can be used in fiber and paint industries, and esters with branched chains are excellent lubricating oils. Moreover, ester bonds are also commo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/04C07C69/157C07C69/78C07C69/618C07C303/36C07C311/06
CPCC07C67/04C07C303/36C07C69/157C07C69/78C07C69/618C07C311/06
Inventor 王兴予朱雪庆高亚茹
Owner NORTHWEST UNIV(CN)
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