JPH01242544A - 1-biphenylylethanol derivative and production thereof - Google Patents

Abstract

NEW MATERIAL:A 1-biphenylylethanol derivative expressed by formula I (A is H, halogen, 1-4C alkyl or 1-4C alkoxyl). EXAMPLE:4'-(1-Hydroxyethyl)-4-benzyloxybiphenyl. USE:Useful as an intermediate for medicines, agricultural chemicals, etc., and particularly as organic electronic materials, especially as an intermediate for liquid crystal compounds. The resultant liquid crystal compositions have excellent properties as ferroelectric liquid crystals. PREPARATION:Acetylbiphenyls expressed by formula II are reduced with a reducing agent capable of reducing only ketones to afford the aimed compound expressed by formula I. The reaction is normally carried out in an organic solvent. Sodium boron hydride, lithium aluminum hydride, etc., are preferably used as the reducing agent in an amount of 2-3times based on the compound expressed by formula II.

Description

Detailed Description of the Invention <Industrial Application Field> The present invention relates to the general formula (I) c, where A is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. The present invention relates to a l-biphenylylethanol derivative represented by (representing alkoxyl V) and a method for producing the same.

It is a new compound that has not been described in any literature, and until now, not only its production method but also its usefulness as a compound have not been known at all.

<Problems to be Solved by the Invention> The 1-biphenylylethanol derivative represented by the general formula (1) is useful as an intermediate for medicines, agricultural chemicals, etc., but it is particularly useful as an intermediate for organic electronic materials, especially liquid crystal compounds. Very important.

For example, the 1-biphenylyl ethanol derivative can be typically converted into a liquid crystal compound by the method shown in the following formula, and the compound has very strong properties as a highly astringent liquid crystal. ing.

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

The 1-biphenylyl ethanol derivative represented by the general formula (1) is a 1-biphenylyl ethanol derivative that reduces only the ketone from the acetyl biphenyls represented by the general formula (11) (wherein A has the same meaning as above). It can be produced by reduction using a reducing agent that can be used.

Acetyl biphenyls (■), which are the starting compounds in this reaction lζ, are, for example, biphenyls represented by the formula and the general formula ((support) (where A has the same meaning as above, and X is a leaving group. The benzyl compound represented by the following can be easily produced by reacting it under basic conditions.

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

Here, the above-mentioned reducing agent may be any one having the ability to selectively reduce only ketones, and examples of the reducing agent in the first ft'l include sodium borohydride, zinc borohydride, aluminum borohydride, etc. Examples include isopropoxide, lithium-tri-t-butoxyaluminum hydride, lithium-tri-S-butylboron hydride, borane, lithium aluminum hydride-silica gel, alkali metal-ammonia, etc., and the second B is aluminum hydride. lithium, aluminum hydride,
Examples include lithium trimethoxyal[nium hydride] and sodium di(methoxyethoxy)aluminum hydride.

The amount of such reducing agent used is based on the raw material acetyl biphenyls (
11) Chemistry #1ililifi or higher, usually 1~
The amount is 10 times, preferably 2 to 8 times.

The organic solvent in this reaction is [11Y alcoholic or ether solvents such as methanol, ethanol, 2-propatol, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, dioxane, dimethoxyethane, and jetoxyethane when using a reducing agent] is preferably used, and when the second group reducing agent is used, in addition to the above-mentioned ether solvents, aromatic hydrocarbons such as toluene and benzene, aliphatic hydrocarbons such as hexane and cyclohexane, etc. are preferably used.

The reaction temperature is arbitrary in the range of -80°C to 150'C, but preferably in the range of -20°C to 90'C.

The reaction time is not particularly limited, and the end point of the reaction can be set at the time when the raw material acetylbiphenyl (U) disappears.

The reaction mixture obtained by such a reduction reaction is subjected to extraction, separation, concentration, distillation, column chromatography, etc. to separate the desired 1-biphenylylethanol derivative (1). can do.

<Effects of the Invention> Thus, according to the method of the present invention, the 1-biphenylylethanol derivative represented by the general formula (1), which is a novel compound, can be produced in good yield from the acetyl biphenyls represented by the general formula (n). The obtained target compound can be advantageously used as a raw material for organic intermediates, particularly liquid crystal material intermediates.

<Example> The present invention will be explained below with reference to Examples.

Example 1 120.95' of 4'-acetyl-4-benzyloxybiphenyl was placed in a four-bottle flask equipped with a stirrer and a thermometer.
(0.4 mol), 100 ml of methanol, and 400 ml of tetrahydrofuran, and added 15.14 P (0.4 mol) of sodium borohydride at 15 to 25°C.
Add it over time.

After incubating at the same temperature for 5 hours, the reaction mixture was poured into ice water.
Extract twice with 500 d of chloroform. After washing the organic layer with water, it was concentrated under reduced pressure to give 4'-(1-hydroxyethyl)-4-benzyloxybiphenyl 117.4P.
(yield 96.5%).

Melting point 161-162°C Example 2 4'-acetyl-4-(4-chlorobenzyloxy) in place of 4'-acetyl-4-benzyloxybiphenyl
The reaction and post-treatment were carried out in the same manner as in Example 1 except for using biphenyl 184.6F. IP (yield 99.8%) was obtained.

Melting point: 170.5-172°C Example 3 A flask similar to that used in Example 1 was charged with 8.8 F (0.1 mol) of lithium aluminum hydride and 200 #/ of anhydrous tetrahydrofuran, and 4'-acetyl -4-(4-methoxybenzyloxy)biphenyl 16.6? (0.05 mol) of tetrahydrofuran 8
00ml solution is gradually added dropwise. After completion of dripping, 80-4
Stir at 0°C for 8 hours. After the reaction is complete, a small amount of ethyl acetate is added to decompose excess lithium aluminum hydride. Thereafter, the reaction solution was poured into 500 ml of IN hydrochloric acid, and 500 d of toluene was added for extraction. The organic layer is washed sequentially with water, 5% sodium bicarbonate solution, and water. After drying the organic layer, the solvent was distilled off under reduced pressure to obtain crude 4I-(1- and droxyethyl)-4-(4-methoxybenzyloxy)biphenyl 16.9F (yield approximately 100%). Ta.

Melting point 185-186°C Example 4 4'-acetyl-4-(4-methoxybenzyloxy)
The reaction and post-treatment were carried out according to Example 8, except that 15.85' (0.05 mol) of 4'-acetyl-4-(4-methylbenzyloxy)biphenyl was used instead of biphenyl.
15.9 f (14 parts) of crude 4'-(1-hydroxyethyl)-4-(4-methylbenzyloxy)biphenyl was obtained.

Melting point: 178-174℃

Claims (2)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, A represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms) 1-biphenylylethanol derivative. (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, A represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms) 2. The method for producing a 1-biphenylylethanol derivative according to claim 1, which comprises reducing acetylpiphenyl.