JPS6366838B2 - - Google Patents
Info
- Publication number
- JPS6366838B2 JPS6366838B2 JP26713384A JP26713384A JPS6366838B2 JP S6366838 B2 JPS6366838 B2 JP S6366838B2 JP 26713384 A JP26713384 A JP 26713384A JP 26713384 A JP26713384 A JP 26713384A JP S6366838 B2 JPS6366838 B2 JP S6366838B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl group
- formula
- chain alkyl
- straight chain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000004973 liquid crystal related substance Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- -1 thienyl acrylate Chemical compound 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
［発明の技術分野］
本発明は室温付近の近い温度範囲で液晶相を示
す新規なチオフエン化合物、その製造方法ならび
に該化合物を含む液晶組成物に関する。
［発明の技術的背景］
液晶は、電場の影響をうけて光散乱、複屈折な
どの光学的性質を顕著に変える特徴を有し、広く
電気光学表示装置に利用される。そのような表示
装置に用いられる液晶に要求される性質は、液晶
温度範囲が広く、かつ低粘性であること、湿気、
熱、光などに対して安定なことである。さらに、
可視光領域で固有の吸収を示さず、着色していな
いことも要求される。このうち液晶温度範囲につ
いては、これが広い場合には、より少ない種類の
液晶物質を混合することで実用に供することが可
能な点で有利であり、また低粘性の場合には液晶
素子の応答時間が短かくなる点で有利である。
［発明の目的］
本発明は広い液晶温度範囲を有する新規なチオ
フエン系化合物であるネマチツク液晶性化合物、
ならびにこの化合物を含む液晶組成物を提供する
ことを目的とする。
［発明の構成］
すなわち本発明の５−ｎ−アルキル−２−チエ
ニルアクリル酸ｐ−ｎ−アルコキシフエニルは、
一般式
（式中、R1は炭素原子数２〜16の直鎖アルキル
基を示し、R2は炭素原子数２〜12の直鎖アルキ
ル基を示す）
で表わされることを特徴し、またその製法は
一般式
（式中、R1は炭素原子数２〜16の直鎖アルキ
ル基を示す）
で表わされる５−ｎ−アルキル−２−チエニル
アクリル酸を塩素化剤と反応させて
一般式
（式中、R1は前記と同じ意味）
で表わされる５−ｎ−アルキル−２−チエニル
アクリル酸クロライドとし、次いでこの酸塩化
物と、一般式
（式中、R2は炭素原子数２〜12の直鎖アルキ
ル基を示す）
で表わされるｐ−ｎ−アルコキシフエノールを
不活性溶媒中で反応させて
一般式
（式中、R1およびR2は前記と同じ意味）
で表わされる化合物を得ること、および
一般式
（式中、R1は炭素原子数２〜16の直鎖アルキ
ル基を示す）
で表わされる化合物と、
一般式
（式中、R2は炭素原子数２〜12の直鎖アルキ
ル基を示す）
で表わされる化合物とをＮ，N′−ジシクロヘ
キシルカルボジイミドの存在下で脱水反応さ
せ、
一般式
（式中、R1およびR2は前記と同じ意味）
で表わされる化合物を得ることを特徴とする。
また本発明の液晶組成物は前記一般式（）で
表わされる化合物を１種以上含むことを特徴とす
る。
式（）〜（）のR1は炭素原子数２〜16の
直鎖アルキル基を示し、このうち特に炭素原子数
２〜12の直鎖アルキル基が好ましい。また式
（）および（）のR2としては炭素原子数２〜
12の直鎖アルキル基があげられ、このうち特に炭
素原子数５〜８の直鎖アルキル基が好ましい。
R1およびR2は同一分子中で同一でもよく、ある
いは相異なつていてもよい。
次に本発明の製造方法について述べる。
製造方法において塩素化剤としては塩化チオ
ニル、三塩化リン、五塩化リンなどが挙げられる
が、特に反応処理の容易さから塩化チオニルが好
ましい。塩化チオニルを用いた場合、式（）の
５−ｎ−アルキル−２−チエニルアクリル酸との
反応は過剰の塩化チオニルを用いて還流させ、反
応後はこの過剰の塩化チオニルを減圧で留去すれ
ばよい。
式（）の５−ｎ−アルキル−２−チエニルア
クリル酸クロライドと式（）のｐ−ｎ−アルコ
キシフエノールとの反応はエチルエーテル、ベン
ゼンなどの不活性溶媒中で行ない、このうち特に
エチルエーテルが好ましい。また反応中に生じる
ハロゲン化水素を系外に除くために、ピリジン、
トリエチルアミンなどの塩基性物質を加えること
が好ましい。反応後、生成物は有機溶媒抽出、水
洗、結晶化等の処理をすることにより目的とする
５−ｎ−アルキル−２−チエニルアクリル酸ｐ−
ｎ−アルコキシフエニルを得ることができる。
また製造方法において、Ｎ，N′−ジシクロ
ヘキシルカルボジイミドは式（）の化合物に対
して通常等モル用い、ピリジンの存在下でジクロ
ロメタン、ジクロロエタン、四塩化炭素等の溶媒
中で脱水反応させる。
本発明に用いる式（）の５−ｎ−アルキル−
２−チエニルアクリル酸はたとえば次に示す方法
で得られる。
第１段階はチオフエン（）に塩化第二錫を触
媒として、酸塩化物（R3COCl、R3は目的とする
化合物（）のR1より炭素原子数が１小さな直
鎖アルキル基を示す。）を反応させて式（）の
化合物を製造することが出来る［J.R.Johnson
and G.E.May、Org.Syn.Col.Vol.、８
（1943）］。
第２段階は式（）の化合物をエチレングリコ
ール系溶剤の存在下でヒドラジン水化物との還流
により還元する。水との共沸混合物を分離し、稀
塩酸で洗浄後、水洗、乾燥、蒸溜等の一連の精製
処理を施して式（）の化合物を製造することが
出来る、［J.Org.Chem.、14638（1949）］。
第３段階は式（）の化合物をエチルエーテル
を溶剤としてフエニルリチウム、Ｎ，Ｎ−ジメチ
ルホルムアミドと室温で反応させたのち、水を加
え、有機層を分離後、水洗、乾燥、蒸溜等の一連
の精製処理を施して式（）の化合物を製造す
る。
第４段階は式（）の化合物をナトリウムの存
在下で酢酸メチルと還流して式（）の化合物を
製造する。反応によつて生成した混合物から式
（）の化合物を単離する必要はなく、酢酸で中
和し、重曹溶液で洗滌後、過剰の酢酸メチルを除
去するだけでよい。
第５段階は第４段階で製造された粗製の式
（）の化合物を加水分解し、反応生成物を含水
エタノールから再結晶させて式（）の化合物を
製造する。
本発明の５−ｎ−アルキル−２−チエニルアク
リル酸ｐ−ｎ−アルコキシフエニルは室温付近の
広い温度範囲でネマチツク液晶を形成する液晶性
化合物であり、チオフエン環を含む液晶性化合物
としては初めてのものである。この化合物は液晶
組成物の配合成分として通常複数の液晶性化合物
と共に用いられる。更に本発明の液晶性化合物中
にはそれ自体では液晶相を示さずとも液晶組成物
の配合成分として有用な物質も含まれる。
次に本発明の主な液晶性化合物の物理特性を第
１表に示す。
[Technical Field of the Invention] The present invention relates to a novel thiophene compound exhibiting a liquid crystal phase in a temperature range close to room temperature, a method for producing the same, and a liquid crystal composition containing the compound. [Technical Background of the Invention] Liquid crystals have the characteristic of significantly changing optical properties such as light scattering and birefringence under the influence of electric fields, and are widely used in electro-optic display devices. The properties required of the liquid crystal used in such display devices are a wide liquid crystal temperature range, low viscosity, humidity,
It is stable against heat, light, etc. moreover,
It is also required that it exhibits no inherent absorption in the visible light region and is not colored. Regarding the liquid crystal temperature range, if it is wide, it is advantageous in that it can be put to practical use by mixing fewer types of liquid crystal materials, and if the viscosity is low, the response time of the liquid crystal element is This is advantageous in that it is shorter. [Object of the invention] The present invention provides a nematic liquid crystal compound which is a novel thiophene compound having a wide liquid crystal temperature range;
The present invention also aims to provide a liquid crystal composition containing this compound. [Structure of the invention] That is, the p-n-alkoxyphenyl 5-n-alkyl-2-thienyl acrylate of the present invention is
general formula (In the formula, R 1 represents a straight chain alkyl group having 2 to 16 carbon atoms, and R 2 represents a straight chain alkyl group having 2 to 12 carbon atoms.) general formula (In the formula, R 1 represents a straight-chain alkyl group having 2 to 16 carbon atoms.) 5-n-alkyl-2-thienyl acrylic acid represented by the formula (In the formula, R 1 has the same meaning as above) 5-n-alkyl-2-thienyl acrylic acid chloride, then this acid chloride and the general formula (In the formula, R 2 represents a straight chain alkyl group having 2 to 12 carbon atoms.) By reacting p-n-alkoxyphenol represented by the following in an inert solvent, the general formula (In the formula, R 1 and R 2 have the same meanings as above.) Obtaining a compound represented by the general formula (In the formula, R 1 represents a straight chain alkyl group having 2 to 16 carbon atoms) and a compound represented by the general formula (In the formula, R 2 represents a straight-chain alkyl group having 2 to 12 carbon atoms) is subjected to a dehydration reaction in the presence of N,N'-dicyclohexylcarbodiimide, and the general formula (In the formula, R 1 and R 2 have the same meanings as above.) It is characterized by obtaining a compound represented by the following. Further, the liquid crystal composition of the present invention is characterized in that it contains one or more compounds represented by the above general formula (). In formulas () to (), R 1 represents a straight-chain alkyl group having 2 to 16 carbon atoms, and among these, a straight-chain alkyl group having 2 to 12 carbon atoms is particularly preferred. In addition, R 2 in formulas () and () has 2 to 2 carbon atoms.
12 straight chain alkyl groups are mentioned, among which straight chain alkyl groups having 5 to 8 carbon atoms are particularly preferred.
R 1 and R 2 may be the same or different in the same molecule. Next, the manufacturing method of the present invention will be described. Examples of the chlorinating agent in the production method include thionyl chloride, phosphorus trichloride, and phosphorus pentachloride, with thionyl chloride being particularly preferred from the viewpoint of ease of reaction treatment. When thionyl chloride is used, the reaction with 5-n-alkyl-2-thienyl acrylic acid of formula () is performed using excess thionyl chloride under reflux, and after the reaction, the excess thionyl chloride is distilled off under reduced pressure. Bye. The reaction between the 5-n-alkyl-2-thienyl acrylic acid chloride of the formula () and the p-n-alkoxyphenol of the formula () is carried out in an inert solvent such as ethyl ether or benzene. preferable. In addition, in order to remove hydrogen halide generated during the reaction from the system, pyridine,
Preferably, a basic substance such as triethylamine is added. After the reaction, the product is extracted with an organic solvent, washed with water, crystallized, etc. to obtain the desired 5-n-alkyl-2-thienyl acrylic acid p-
n-alkoxyphenyl can be obtained. In the production method, N,N'-dicyclohexylcarbodiimide is usually used in equimolar amounts to the compound of formula (), and dehydration is carried out in a solvent such as dichloromethane, dichloroethane, carbon tetrachloride, etc. in the presence of pyridine. 5-n-alkyl- of formula () used in the present invention
2-thienyl acrylic acid can be obtained, for example, by the method shown below. The first step is to form an acid chloride (R 3 COCl, where R 3 represents a linear alkyl group having one carbon atom smaller than R 1 of the target compound ()) using thiophene () and stannic chloride as a catalyst. ) can be reacted to produce a compound of formula () [JRJohnson
and GEMay, Org.Syn.Col.Vol., 8
(1943)]. In the second step, the compound of formula () is reduced by refluxing with hydrazine hydrate in the presence of an ethylene glycol solvent. The compound of formula () can be produced by separating the azeotropic mixture with water, washing with dilute hydrochloric acid, and performing a series of purification treatments such as washing with water, drying, and distillation [J.Org.Chem. 14638 (1949)]. In the third step, the compound of the formula () is reacted with phenyllithium and N,N-dimethylformamide at room temperature using ethyl ether as a solvent, water is added, the organic layer is separated, and then washed with water, dried, distilled, etc. A series of purification treatments are performed to produce the compound of formula (). The fourth step is to reflux the compound of formula () with methyl acetate in the presence of sodium to produce a compound of formula (). It is not necessary to isolate the compound of formula () from the mixture produced by the reaction, it is only necessary to neutralize it with acetic acid and remove excess methyl acetate after washing with a sodium bicarbonate solution. In the fifth step, the crude compound of formula () produced in the fourth step is hydrolyzed and the reaction product is recrystallized from aqueous ethanol to produce the compound of formula (). The p-n-alkoxyphenyl 5-n-alkyl-2-thienyl acrylate of the present invention is a liquid crystal compound that forms nematic liquid crystals in a wide temperature range around room temperature, and is the first liquid crystal compound containing a thiophene ring. belongs to. This compound is usually used together with a plurality of liquid crystal compounds as a compounding component of a liquid crystal composition. Furthermore, the liquid crystalline compounds of the present invention also include substances that do not exhibit a liquid crystal phase by themselves but are useful as components of liquid crystal compositions. Next, Table 1 shows the physical properties of the main liquid crystal compounds of the present invention.
【表】
←
[Table] ←
【表】
←
[Table] ←
Claims (1)
基を示し、R2は炭素原子数２〜12の直鎖アルキ
ル基を示す） で表わされることを特徴とする５−ｎ−アルキル
−２−チエニルアクリル酸ｐ−ｎ−アルコキシフ
エニル。 ２ R1が炭素原子数２〜12の直鎖アルキル基で
あり、R2が炭素原子数５〜８の直鎖アルキル基
である特許請求の範囲第１項記載の５−ｎ−アル
キル−２−チエニルアクリル酸ｐ−ｎ−アルコキ
シフエニル。 ３ 一般式 （式中、R1は炭素原子数２〜16の直鎖アルキル
基を示す） で表わされる５−ｎ−アルキル−２−チエニルア
クリル酸を塩素化剤と反応させて 一般式 （式中、R1は前記と同じ意味） で表わされる５−ｎ−アルキル−２−チエニルア
クリル酸クロライドとし、次いでこの酸塩化物
と、一般式 （式中、R2は炭素原子数２〜12の直鎖アルキル
基を示す） で表わされるｐ−ｎ−アルコキシフエノールを不
活性溶媒中で反応させて 一般式 （式中、R1および2は前記と同じ意味） で表わされる化合物を得ることを特徴とする５−
ｎ−アルキル−２−チエニルアクリル酸ｐ−ｎ−
アルコキシフエニルの製造方法。 ４ R1が炭素原子数２〜12の直鎖アルキル基で
あり、R2が炭素原子数５〜８の直鎖アルキル基
である特許請求の範囲第３項記載の方法。 ５ 一般式 （式中、R1は炭素原子数２〜16の直鎖アルキル
基を示す） で表わされる化合物と、 一般式 （式中、R2は炭素原子数２〜12の直鎖アルキル
基を示す） で表わされる化合物とをＮ，N′−ジシクロヘキ
シルカルボジイミドの存在下で脱水反応させ、 一般式 （式中、R1およびR2は前記と同じ意味） で表わされる化合物を得ることを特徴とする５−
ｎ−アルキル−２−チエニルアクリル酸ｐ−ｎ−
アルコキシフエニルの製造方法。 ６ R1が炭素原子数２〜12の直鎖アルキル基で
あり、R2が炭素原子数５〜８の直鎖アルキル基
である特許請求の範囲第５項記載の方法。 ７ 一般式 （式中、R1は炭素原子数２〜12の直鎖アルキル
基を示し、R2は炭素原子数５〜８の直鎖アルキ
ル基を示す） で表わされる化合物を１種以上含むことを特徴と
する液晶組成物。[Claims] 1. General formula (wherein, R 1 represents a straight chain alkyl group having 2 to 16 carbon atoms, and R 2 represents a straight chain alkyl group having 2 to 12 carbon atoms) p-n-alkoxyphenyl alkyl-2-thienyl acrylate. 2. 5-n-alkyl-2 according to claim 1, wherein R 1 is a straight-chain alkyl group having 2 to 12 carbon atoms, and R 2 is a straight-chain alkyl group having 5 to 8 carbon atoms. - p-n-alkoxyphenyl thienyl acrylate. 3 General formula (In the formula, R 1 represents a straight-chain alkyl group having 2 to 16 carbon atoms.) 5-n-alkyl-2-thienyl acrylic acid represented by the formula (In the formula, R 1 has the same meaning as above) 5-n-alkyl-2-thienyl acrylic acid chloride, then this acid chloride and the general formula (In the formula, R 2 represents a straight chain alkyl group having 2 to 12 carbon atoms.) By reacting p-n-alkoxyphenol represented by the following in an inert solvent, the general formula (wherein R 1 and 2 have the same meanings as above)
n-alkyl-2-thienyl acrylic acid p-n-
Method for producing alkoxyphenyl. 4. The method according to claim 3, wherein R1 is a straight chain alkyl group having 2 to 12 carbon atoms, and R2 is a straight chain alkyl group having 5 to 8 carbon atoms. 5 General formula (In the formula, R 1 represents a straight chain alkyl group having 2 to 16 carbon atoms) and a compound represented by the general formula (In the formula, R 2 represents a straight-chain alkyl group having 2 to 12 carbon atoms) is subjected to a dehydration reaction in the presence of N,N'-dicyclohexylcarbodiimide, and the general formula (wherein R 1 and R 2 have the same meanings as above)
n-alkyl-2-thienyl acrylic acid p-n-
Method for producing alkoxyphenyl. 6. The method according to claim 5, wherein R1 is a straight chain alkyl group having 2 to 12 carbon atoms, and R2 is a straight chain alkyl group having 5 to 8 carbon atoms. 7 General formula (In the formula, R 1 represents a straight chain alkyl group having 2 to 12 carbon atoms, and R 2 represents a straight chain alkyl group having 5 to 8 carbon atoms.) A liquid crystal composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26713384A JPS61143375A (en) | 1984-12-17 | 1984-12-17 | 5-n-alkyl-2-thienylacrylic acid p-n-alkoxyphenyl and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26713384A JPS61143375A (en) | 1984-12-17 | 1984-12-17 | 5-n-alkyl-2-thienylacrylic acid p-n-alkoxyphenyl and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61143375A JPS61143375A (en) | 1986-07-01 |
| JPS6366838B2 true JPS6366838B2 (en) | 1988-12-22 |
Family
ID=17440532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26713384A Granted JPS61143375A (en) | 1984-12-17 | 1984-12-17 | 5-n-alkyl-2-thienylacrylic acid p-n-alkoxyphenyl and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61143375A (en) |
-
1984
- 1984-12-17 JP JP26713384A patent/JPS61143375A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61143375A (en) | 1986-07-01 |
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