JP2512958B2 - 1-biphenylylethanol derivative and process for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a compound represented by the general formula (I): (In the formula, R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms) and a method for producing the 1-biphenylylethanol derivative.

<Prior Art> The biphenyl derivative represented by the general formula (I) is a novel compound that has not been described in any literature, and conventionally, not only its production method but also its usefulness as a compound has not been known at all. .

<Problems to be Solved by the Invention> The 1-biphenylylethanol derivative represented by the general formula (I) is very important as an intermediate for medicines, agricultural chemicals, etc., especially as an organic electronic material, especially as an intermediate for liquid crystal compounds. Is.

For example, the 1-biphenylylethanol derivative can be typically introduced into a liquid crystal compound by a method represented by the following formula, and the compound is very excellent as a ferroelectric liquid crystal.

<Means for Solving Problems> The present invention provides such a novel and useful 1-biphenylylethanol derivative represented by the general formula (I).

The 1-biphenylylethanol derivative represented by the general formula (I) has the general formula (I) (In the formula, R has the same meaning as described above.) The acetylbiphenyls can be produced by reducing with a reducing agent capable of reducing only the ketone.

Acetylbiphenyls (II), which are the raw material compounds in this reaction, are represented by the formula The cyanobiphenyls represented by
It can be easily synthesized by solvolysis in the presence of an acid or a base in 10 alcohols.

The reduction reaction of acetylbiphenyls (II) is usually carried out in an organic solvent in the presence of a reducing agent capable of reducing only a ketone.

Here, the reducing agent may be any agent having the ability to selectively reduce only a ketone, and examples of the reducing agent include sodium borohydride, zinc borohydride, aluminum isopropoxide, and lithium-trioxide. Examples thereof include -t-butoxyaluminum hydride, lithium-tri-s-butylboron hydride, borane, lithium aluminum hydride-silica gel, alkali metal-ammonia and Raney nickel.

The reducing agent is used in a stoichiometric amount or more, usually 1 to 10 times, and preferably 2 to 3 times the amount of the starting acetylbiphenyls (II).

As the organic solvent in this reaction, alcohol-based or ether-based solvents such as methanol, ethanol, 2-propanol, methyl cellosolve, ethyl cellosolve, dimethoxyethane and diethoxyethane are preferably used.

Here, when an alcoholic solvent is used as the solvent, the ester portion of the starting material acetylbiphenyls (II) undergoes solvolysis to yield the target compound of the formula (I), Although the purity and the like may be lowered, the side reaction can be suppressed by adding a solvent inert to the reaction such as chloroform and dichloromethane. Further, the addition of such a solvent increases the solubility of the raw material acetylbiphenyls (II), which is also advantageous in terms of volume efficiency during the reaction.

The reaction temperature is arbitrary in the range of -30 ° C to 100 ° C, but is preferably in the range of -20 ° C to 90 ° C.

The reaction time is not particularly limited, and the time point at which the raw material acetylbiphenyls (II) disappears can be the end point of the reaction.

The target 1-biphenylylethanol derivative (I) is separated by subjecting the reaction mixture obtained by such a reduction reaction to operations such as extraction, liquid separation, concentration, distillation, and column chromatography treatment. You can

<Effect of the Invention> Thus, according to the method of the present invention, the 1-biphenylylethanol derivative represented by the general formula (I) is obtained in good yield from the acetylbiphenyls represented by the general formula (II). The target compound can be advantageously used as an organic intermediate, especially as a raw material for a liquid crystal material intermediate.

<Example> Hereinafter, the present invention will be described with reference to Examples.

Example 1 4′-in a four-necked flask equipped with a stirrer and a thermometer.
Ethyl acetyl-4-biphenylcarboxylate 32.2 g (0.1
(2 mol), ethanol (50 ml) and chloroform (150 ml) were charged, and sodium borohydride 2.3 g (0.06
Mol) over 10 minutes.

After keeping at the same temperature for 2 hours, the reaction mixture is poured into ice water and extracted twice with 200 ml of ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure to give 30.8 g of ethyl 4 '-(1-hydroxyethyl) -4-biphenylcarboxylate (yield 95
%) Was obtained.

Melting point 69.5 ° C. Example 2 Reaction and post-treatment were conducted in the same manner as in Example 1 except that ethyl 4′-acetyl-4-biphenylcarboxylate was replaced with pentyl 4′-acetyl-4-biphenylcarboxylate to give 4 36.4 g (yield 97%) of pentyl '-(1-hydroxyethyl) -4-biphenylcarboxylic acid was obtained.

 Melting point 65.2 ℃

Claims (2)

(57) [Claims] 1. A general formula (In formula, R shows a hydrogen atom or a C1-C10 alkyl group.) 1-biphenylyl ethanol derivative shown by these. 2. The general formula (In the formula, R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms). A general formula characterized by reducing acetylbiphenyls with a reducing agent capable of reducing only a ketone. (In the formula, R has the same meaning as described above.) A method for producing a 1-biphenylylethanol derivative represented by: