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Method for synthesizing phenyl acetate derivatives

A technology of phenyl acetates and synthetic methods, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of expensive catalysts, restricting industrial development, and difficult storage, etc., and achieve substrate expansion Wide-ranging, lucrative, and easy-to-manage effects

Active Publication Date: 2019-04-19
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the acetyl chloride used in this method is a highly hazardous chemical, flammable, explosive, and expensive
In addition, acetic anhydride and acetyl chloride are not easy to store and are easily hydrolyzed into acetic acid in humid air. Therefore, the reaction system needs to be strictly controlled under anhydrous conditions.
In addition, in recent years, the newly developed catalytic systems such as ionic liquids and noble metals are important supplementary methods for the synthesis of phenyl acetate derivatives, but the catalysts are expensive, which may limit the industrial development of this method.

Method used

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  • Method for synthesizing phenyl acetate derivatives
  • Method for synthesizing phenyl acetate derivatives
  • Method for synthesizing phenyl acetate derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of acetic acid-2-naphthyl ester

[0016]

[0017] Add β-naphthol (43.2 mg), potassium thioacetate (102.6 mg), Cu(OAc) to a 25 mL reaction tube 2 (12.0 mg), acetonitrile (2 mL), and magnetically stirred at 80° C. for 4 hours. After the reaction is finished, extract with ethyl acetate, collect the organic phase, evaporate most of the solvent under reduced pressure, and use petroleum ether: ethyl acetate (10:1) as eluent to carry out column chromatography for the remaining mixed solution. After purification, the target product was obtained as white needle crystals, 51 mg, yield 92%.

[0018] Its NMR data are as follows:

[0019] 1 H NMR (300MHz, CDCl 3 )δ=7.91~7.87(m,3H),7.61(s,1H),7.53-7.51(t,2H),7.30-7.27(t,3H),2.40(s,3H);

[0020] 13 C NMR (75MHz, CDCl 3 ) δ = 169.62, 146.70, 134.75, 128.15, 126.87, 126.39, 126.13, 125.50, 125.14, 121.22, 118.18, 21.09.

Embodiment 2

[0021] Embodiment 2: the synthesis of acetic acid-1-naphthyl ester

[0022]

[0023] Add α-naphthol (43.2 mg), potassium thioacetate (102.6 mg), Cu(OAc) to a 25 mL reaction tube 2 (12.0 mg), acetonitrile (2 mL), and magnetically stirred at 80° C. for 4 hours. After the reaction is finished, extract with ethyl acetate, collect the organic phase, evaporate most of the solvent under reduced pressure, and use petroleum ether: ethyl acetate (10:1) as eluent to carry out column chromatography for the remaining mixed solution. After purification, the target product was obtained as colorless needle crystals, 46 mg, and the yield was 83%.

[0024] Its NMR data are as follows:

[0025] 1 H NMR (300MHz, CDCl 3 )δ=7.93~7.91(m,2H), 7.81~7.78(m,1H), 7.58~7.49(m,3H), 7.31~7.29(d,1H), 2.51(s,3H);

[0026] 13 C NMR (75MHz, CDCl 3 ) δ = 169.78, 148.42, 133.85, 131.56, 129.53, 127.88, 127.75, 126.67, 125.82, 121.25, 118.65, 21.30.

Embodiment 3

[0027] Embodiment 3: the synthesis of acetic acid-2-methylphenyl ester

[0028]

[0029] Add o-cresol (32.4 mg), potassium thioacetate (102.6 mg), Cu(OAc) to a 25 mL reaction tube 2 (12.0 mg), acetonitrile (2 mL), and magnetically stirred at 80° C. for 4 hours. After the reaction is finished, extract with ethyl acetate, collect the organic phase, evaporate most of the solvent under reduced pressure, and use petroleum ether: ethyl acetate (10:1) as eluent to carry out column chromatography for the remaining mixed solution. After purification, the target product was obtained as a white solid, 27 mg, and the yield was 60%.

[0030] Its NMR data are as follows:

[0031] 1 H NMR (300MHz, CDCl 3 )δ=7.27~7.17(m,3H),7.03(d,J=7.6Hz,1H),2.35(d,J=2.5Hz,3H),2.2(s,3H);

[0032] 13 C NMR (75MHz, CDCl 3 ) δ = 169.37, 149.40, 131.20, 130.16, 127.00, 126.13, 121.92, 20.89, 16.20.

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Abstract

The invention discloses a method for synthesizing phenyl acetate derivatives. The method of the invention comprises the following steps: 1, adding a phenol derivative, potassium thioacetate, copper acetate and acetonitrile to a reaction tube, and tightening the bottle stopper of the reaction tube, and magnetically stirring at 80 DEG C and reacting for 4 h; and 2, extracting with ethyl acetate, mixing organic phases, removing most of the solvent by reduced pressure distillation, and carrying out column chromatography separation and purification on residual mixed liquor by using petroleum etherand ethyl acetate at the volume ratio of 10:1 as a leacheate so as to obtain a target product. By using a phenol derivative as the raw material and using stable potassium thioacetate, which is cheap and easily available and is easy to operate, as an acetylation reagent, a series of phenyl acetate derivatives are efficiently synthesized, and the yield is considerable.

Description

technical field [0001] The invention belongs to the field of organic synthesis intermediates, and relates to a synthesis method for acetylating phenolic compounds by using potassium thioacetate as an acetylating reagent to obtain phenyl acetate derivatives. Background technique [0002] Phenyl acetate derivatives are important intermediates in organic synthesis and can be widely used in chemical industry, materials, pesticides and other fields. In addition, as important drug intermediates, phenyl acetate derivatives can be further converted into a mixture of o-hydroxyacetophenone and p-hydroxyacetophenone to treat jaundice hepatitis, cholecystitis and other diseases. The synthetic method of the phenyl acetate derivatives that literature has reported mainly contains two kinds: 1. phenol and acetic anhydride are synthesized under the catalysis of alkali or acid, though this method has the feature that yield is high, but catalyzer is strong acid or strong base, It is highly co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/157
CPCC07C67/08C07C69/157
Inventor 张洁雨柯求敏田飞涛江背姬长安张玲严国兵
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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