JPS6078972A - Ester compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R is 1-10C alkyl, alkoxyl or CN; formula II is benzene ring or cyclohexane ring; X is CN, H, halogen, 1- 10C alkyl or alkoxyl; Y and Z are H when formula II is cyclohexane ring, and CN, H, halogen, 1-10C alkyl or alkoxyl when formula II is benzene ring). EXAMPLE:5-Hexyl-2-pyrimidinyl p-n-hexyloxybenzoate. USE:A material for liquid crystal display elements manufacturable from well- known materials in high yield. PREPARATION:A compound expressed by formula III is esterified with a compound expressed by formula IV or V by the conventional method to give easily the compound expressed by formula I . The mixing of the resultant compound expressed by formula I with another liquid crystal compound permits the reduction of driving voltage of liquid crystal cells using the above-mentioned composition.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel organic compounds, and more particularly to novel ester compounds.

Conventionally, esters of p-substituted phenols such as benzoic acid, p-substituted benzoic acid, cyclohexanecarboxylic acid, and 4-[substituted cyclohexane-1-carboxylic acid] can be used to produce various liquid crystals by utilizing their liquid crystal properties. Many of these materials are highly valued as materials for display devices and the like.

However, the raw material for obtaining this type of ester is p.
-Substituted phenol is not easily available and can be obtained from phenol through several reaction steps, but it has a reaction specificity with % benzene compounds and the yield decreases significantly, so it is an expensive raw material. It becomes.

The present inventors have investigated ω1 of anisotropic ester compounds using heteroaromatic hydroxide as a raw material instead of pmm suphenol, and have found that esters of 5-okiki-pyrimidinol can be synthesized with high yield, They have also found that it is extremely useful as an embodiment of a liquid crystal display element, leading to the present invention.

That is, an object of the present invention is to provide a novel ester compound that can be used for the same purposes as conventional phenyl esters and can be produced at a much higher yield than sycamo phenyl esters.

The first aspect of the present invention is the general formula (wherein R represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or a cyano group, ■ represents a benzene I or cyclohexane ring, and X represents a cyano group or a hydrogen group. ,
It represents a halogeno group or an alkyl group or alkoxy group having 1 to 10 carbon atoms, and when ■ is a cyclohexane ring, Y or 2 represents an aqueous group; when ■ is a benzene ring, it represents a cyano group, a hydrogen group, a halogeno group, or Carbon number 1-10
represents an alkyl group or an alkoxy group. ) is an ester compound.

The second aspect of the present invention is a liquid crystal composition characterized by containing at least one ester compound represented by the general formula [■] (wherein R2O, X, Y and 2 each have the above-mentioned meanings). It is a thing.

The raw material for the ester compound in the present invention is not an expensive one such as p-substituted phenol, but can be easily obtained from urea and aldehyde.

That is, as shown in the chemical reaction formula, it is synthesized through the route of the following formula.

R-OH20HO+(OH3)2NCIIO→(OH3
)2NOH÷Q-QHO(1)(U) Reaction formula (1) is a reaction called a virsu+eir reaction, and is not complicated or difficult. Moreover, reaction formula (2) can also be easily synthesized by a conventional condensation reaction.

The ester compound of the formula (1) of the present invention is a conventional ester between a 5-substituted-2-pyrimidinol of the formula [...] and a carboxylic acid of the formula [for] or a carboxylic acid chloride of the formula (IV3). easily obtained by chemical reaction.

(ill) (IV) Many of the ester compounds of the present invention exhibit a liquid crystal phase, and by mixing these with other liquid crystal compounds, the composition q1
The driving voltage of a quasi-crystalline cell using 21 can be lowered. Furthermore, ester compounds that do not show the same effect as those shown in Table 1 can also be added to liquid crystal compositions to exhibit similar effects.

EXAMPLES The present invention will be specifically explained below with reference to Examples, but the present invention is not limited thereto.

Example 1 p-n-hexyloxy7benzo[-4-hexyl-2-
Bimidinyl ester commercially available urea 6. Of (0.1 mol) and α-n-hexyl-β-dimethylaminoacrolein 18.3t
(0.1 mol) was mixed with ethanol-k7Q+d and while stirring, Salt Preparation 1[50-] was added dropwise to this #liquid.

After adding concentrated hydrochloric acid dropwise, the reaction solution was heated under reflux for 1.5 hours, and the reaction solution was
The mixture was allowed to stand at ℃ for 16 hours to precipitate crystals.

The crystals were separated from P and dried, and 20t of 5-n-hexyl-2
-Pyrimidinol hydrochloride was obtained (yield: 49716).

This hydrochloride was dissolved in 3011 t of pure water, and 2N-NaO
When the pH was adjusted to between 6 and 7 by adding aqueous H solution, pale yellow crystals were precipitated. Separate the kernel crystals into 1 - hebutane -
Recrystallize $11 using a mixed solvent of methanol to obtain 5-
n-hexyl-2-pyrimidinol 8.4? (yield: 48 cm).

1.8 f of 5-n-hexyl-2-pyrimidinol
(1'Ommol) to pyridine 2-MW) and added 2.4 t of -p-n-hexyloxybenzoin chloride to this.
(10 mmoJ) of Toluev 30a+ was added dropwise to the yukata, and the mixture was stirred at a temperature of 50° C. for 4 hours.

After that, toluene 50- was added to the reaction solution and extraction was performed to create a toluene layer t-6N-4OA! It was washed twice with a 30ml water bath, and further washed five times with 40ml of a 2N NaOH aqueous solution, and then washed with pure water until the pH of the aqueous layer reached 7. After drying the toluene layer with anhydrous Na2SO4, the toluene was distilled off to obtain crude crystals 3.1? (Yen = 81%) was obtained. This crude crystal is treated with activated alumina chromatography (solvent toluene)! # and then recrystallized with ethanol to obtain p
-4-n-hexyl-n-hexyloxybenzoate-
2.2t (yield 5B%) of 2-pyrimidinyl was obtained.

This compound shows liquid crystallinity, and the phase transition point is ON point 28.4
℃, NI point u35℃.

Examples 2 to 4 Compounds synthesized according to Example 1Vc, their yields, and physical property values are shown in Table 1, including the results of Example 1.

Table 1 *0 in the phase transition temperature column. The character represents a distorted crystal, a nematic phase, and an isotropic tia phase, and the symbol below it indicates the presence of that phase, and the number following the symbol indicates the transition from that phase to the phase to the right. Indicates the wet layer. - indicates that the phase does not exist.

Written amendment to the above procedure dated November 7, 1980 Manabu Shiga, Commissioner of the Patent Office1, Indication of the case, 1987 Patent Application No. 1879972, Name of the invention: Ester compound3, Person making the amendment Relationship with the case Patent application 3-6-32 Nakanoshima, Kita-ku, Osaka-shi, Osaka (530)
(207) Chisso Corporation Representative Sadao Nogi 4, Agent 2-8-1 Shinjuku, Shinjuku-ku, Tokyo (160) 5 Date of amendment order (voluntary amendment) 6 Number of inventions increased by amendment None 7, Detailed explanation of the invention column 8 of the specification subject to amendment, Contents of amendment (1) Specification No. 6, lines 11-12, r p -n-hexyloxybenzoate-4-hexyl- rp-n-hexyloxybenzoic acid-5
-hexyl-2-pyrimidinyl ester".

(2) The same book, page 7, bottom line to page 8, line 2, rp-n-hexyloxybenzoate-4-hexyl-2-pyrimidinylJerpn-hexyloxybenzoate-5-hexyl-2-pyrimidinyl. I am corrected.

that's all

Claims (1)

[Scope of Claims] (In the formula, R represents an alkyl group or alkoxy group having carbon a1 to a10, or a cyan group, ■ represents a benzene ring or a cyclohexane ring, and X represents a cyano group, a hydrogen group, a halogeno group, or SY or 2 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms; if ■ is a cyclohexane ring, it represents a hydrogen group; if ◇) is a benzene ring, it represents a cyano group, a hydrogen group, a halogeno group, or a cyano group having 1 to 1 carbon atoms; l
Alkyl group or alkoxy group f of O: represents. ) is an ester compound shown by (2) General formula. (In the formula, R represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or a cyano group, ■ represents a benzene ring or a cyclohexane ring, and X represents a cyano group, a hydrogen group, a halogeno group, or a cyano group having 1 to 10 carbon atoms. 10 alkyl group or alkoxy group, Y or 2 represents a hydrogen group when ■ is a cyclohexane ring, and when ■ is a benzene ring, it represents a cyano group, hydrogen group, halogeno group, or a carbon number of 1 to 1
0 represents an alkyl group or an alkoxy group. ) A liquid crystal composition comprising at least one ester compound represented by the following.