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1-acetoxy-3-(substituted phenyl) propen compounds preparation method

A technology for acetoxy and benzene compounds, applied in the field of preparation of 1-acetoxy-3-propene compounds, which can solve the problems of low and unsatisfactory yields of target compounds

Active Publication Date: 2006-02-22
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, when titanium tetrachloride was used as the Lewis acid, the yield of the target compound was 46.2%, and when boron trifluoride ether complex was used, the yield of the target compound was 2.3%, in either case , the yields of the target compounds are all low, which is unsatisfactory

Method used

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preparation example Construction

[0046] The 1-acetoxy-3-(substituted phenyl)propene compound prepared according to the preparation method of the present invention is based on the asymmetric carbon atom and / or double bond contained in the compound represented by the above general formula (I), of course Contains various stereoisomers.

[0047] In order to prepare the 1-acetoxy-3-(substituted phenyl) propene compound of the present invention, the method of the present invention comprises: in the presence of the specific catalyst described in detail later, making the compound obtained from the above general formula (IV) and (V) One selected from the group of benzene compounds shown is reacted with the alkenylene diacetate represented by the above general formula (VI). The benzene compound of formula (IV) and (V) corresponds to the substituted phenyl represented by general formula (II) and (III), and the alkenylene diacetate represented by general formula (VI) is in general formula (I) In combination with the A b...

Embodiment 1

[0085] In an argon atmosphere, 1,2-methylenedioxybenzene (6.83 g, 56.0 mmol) and 3,3-diacetoxy- A mixed solution of 2-methylpropene (1.05 g, 5.6 mmol) was mixed with boron trifluoride diethyl ether complex (74 mg, 0.52 mmol). The mixture was stirred at 23° C. for 1 hour, ethyl acetate (50 ml) was mixed into the resulting reaction solution, the organic layer formed in the reaction solution was separated, washed three times with water (50 ml), and dried over anhydrous sodium sulfate , and the solvent was distilled off. The residue was subjected to silica gel column chromatography, and 1-acetoxy-2-methyl-3-(3,4-methylenedioxy 1.15 g of phenyl)propene was collected as white crystals. The isolated yield of the obtained target compound was 88%.

[0086] The physical property values ​​of 1-acetoxy-2-methyl-3-(3,4-methylenedioxyphenyl)propene are expressed as follows:

[0087] 1 H-NMR (300MHz, CDCl 3 ) δ = 1.56 (3H, d, J = 1.5Hz), 2.15 (3H, s), 3.18 (2H, s), 5.92 (2H, s), 6.63 (...

Embodiment 2

[0094] In an argon atmosphere, 1,2-methylenedioxybenzene (6.83 g, 55.97 mmol) and 3,3-diacetoxy- A mixed solution of 2-methylpropene (0.96 g, 4.88 mmol) was mixed with a boron trifluoride diethyl ether complex (77 mg, 0.54 mmol). The mixed solution was stirred at 23° C. for 1 hour, acetonitrile (100 ml) was mixed with the obtained reaction solution, the mixture was subjected to high performance liquid chromatography, and the reaction solution was analyzed by the absolute calibration curve method. As a result, the yield of 1-acetoxy-2-methyl-3-(3,4-methylenedioxyphenyl)propene was 97.1%. In addition, 5.86 g of unreacted 1,2-methylenedioxybenzene was contained in the reaction liquid.

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Abstract

The compounds represented by the formula (I) are produced by reacting benzene compound of the formula (IV) or (V) with alkenylidene diacetate of the formula (VI) in the presence of a catalyst comprising one or more members selected from (a) halogenated boron compounds, (b) triflate compounds of Group 11 elements, (c) halogenated compounds of Group 12 elements, and (d) triflate and halogenated compounds of tin and atomic numbers 58 and 66 to 71 elements. R<1>, R<2> = H or C1 - C10 alkyl group A = Substituted phenyl group corresponding to a compound of formula (IV) or (V), R<3>, R<4> = H or C1 - C4 alkyl group, m = 0 or 1 - 4, n = 1 to 5, k = 1 or 2.

Description

technical field [0001] The present invention relates to a preparation method of 1-acetoxy-3-(substituted phenyl)propene compound. In more detail, the present invention relates to a method for preparing a 1-acetoxy-3-(substituted phenyl)propene compound having a phenyl group substituted with an alkoxy group or an alkanedioxy group at the 3-position . [0002] The 1-acetoxy-3-(substituted phenyl)propene compound prepared by the method of the present invention is useful as an intermediate of spices, pharmaceuticals, pesticide products, and other organic synthetic drugs. Background technique [0003] As a synthetic method of 1-acetoxy-3-(substituted phenyl)propene compound, in Bull, Soc, Chim, France, 1961, P1194-1198, it is disclosed in tetrafluoroethylene activated by boron trifluoride ether coordination compound Synthesis of 1-acetoxy-3-(3,4-dimethoxyphenyl)propene by reacting 1,2-dimethoxybenzene with alkenylene diacetate in the presence of titanium chloride Methods. How...

Claims

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Application Information

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IPC IPC(8): C07D317/54C07C67/293C07C69/157
Inventor 白井昌志吉田佳弘贞池慎一郎
Owner UBE IND LTD
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