JPS58208241A - Preparation of 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound - Google Patents
Preparation of 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compoundInfo
- Publication number
- JPS58208241A JPS58208241A JP57091048A JP9104882A JPS58208241A JP S58208241 A JPS58208241 A JP S58208241A JP 57091048 A JP57091048 A JP 57091048A JP 9104882 A JP9104882 A JP 9104882A JP S58208241 A JPS58208241 A JP S58208241A
- Authority
- JP
- Japan
- Prior art keywords
- trans
- alkylcyclohexyl
- bis
- bromobenzene
- biphenyl compound
- 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.)
- Pending
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は４．４′−ビス−（トランス−４−アルキルシ
クロヘキシル）−ビフェニル化合物の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compounds.
４．４′−ビス−（トランス−４−アルキルシクロへキ
シル）−ビフェニル化合物は非常に広い液晶相を持ち、
液晶表示素子への応用、例えば極低温域での高速応答が
要求される車載用などの非常にきびしい条件を克服する
液晶材料として注目されている。4.4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound has a very broad liquid crystal phase,
It is attracting attention as a liquid crystal material that can be applied to liquid crystal display devices, such as those used in automobiles that require high-speed response at extremely low temperatures.
従来の製造法として、特許出願公開昭和５６−１０５１
２０号に報告されているが、この製造法では４−（）ラ
ンス−４−アルキルシクロへキシル） −４１−ブロム
ビフェニルのグリニヤール試薬と、４−アルキルシクロ
ヘキサノンの反応で、目的とする４、４７−ビス−（ト
ランス−４−アルキルシクロヘキシル）−ビフェニル化
合物を得るが、この方法ではシス及びトランス異性体の
生成があり、反応後にこれらを異性体、あるいは分離す
ることが困難である。またこの方法では反応終了後に水
素添加操作があり、これは工業的に多量の反応を行なう
際の障害となる。As a conventional manufacturing method, the patent application was published in 1982-1051.
20, this production method involves the reaction of 4-()lans-4-alkylcyclohexyl)-41-brombiphenyl with a Grignard reagent and 4-alkylcyclohexanone to produce the desired 4,47 Although a -bis-(trans-4-alkylcyclohexyl)-biphenyl compound is obtained, this method produces cis and trans isomers, and it is difficult to separate these into isomers or separate them after the reaction. Furthermore, this method requires a hydrogenation operation after the reaction is completed, which poses an obstacle when carrying out a large-scale reaction industrially.
本発明はかかる欠点を除くものであり、その目的は安全
かつ容易にトランス体だけを得る方法を提供することで
ある。The present invention aims to eliminate such drawbacks, and its purpose is to provide a method for safely and easily obtaining only the trans isomer.
本発明では一般式
Ｒ１−＠−＠−Ｂｒ （式中Ｒ１は水素または炭素数１
〜１０個の直鎖アルキル基を示す。）で表わされるＰ−
（トランス−イーアルキルシクロヘキシル）−プロムベ
ンゼント、一般式
Ｒ１１−〇−ｏ−Ｂｒ （式中Ｒ２は水素または炭素数
１〜１０個の直鎖アルキル基を示す。）で表わされるＰ
−（）ランス−４−アルキルシクロヘキシル）−ブロム
ベンゼンの両者を一般式
ＮｒｘａｚａＬ （ｘ、ｘ は配位子で、トリフェニ
ルホスフィン、１．３−ビス−（ジフェニルホスフィノ
）プロパン、１．２−ビス−（ジフェニルホスフィノ）
エタンを示す。）で表わされるニッケルーホスフィン錯
体を触媒として、グリニヤール反応により縮合させ、４
．４’−ビス−（トランス−４−アルキルシクロヘキシ
ル）−ビフェニル化合物を得る。この製造法では原料と
して公知の方法で得られるトランス体を用いるため、生
成物はトランス−トランス体となり、反応終了後の異性
体の分離精製は必要なくなる。また水素添加操作がない
ため、安全でありかつ工程の短縮ができる。In the present invention, the general formula R1-@-@-Br (wherein R1 is hydrogen or has 1 carbon number
Indicates ~10 straight chain alkyl groups. ) represented by P-
(trans-eealkylcyclohexyl)-probenzene, P represented by the general formula R11-o-o-Br (wherein R2 represents hydrogen or a straight-chain alkyl group having 1 to 10 carbon atoms)
-()rans-4-alkylcyclohexyl)-bromobenzene with the general formula NrxazaL (x, x are ligands, triphenylphosphine, 1.3-bis-(diphenylphosphino)propane, 1.2- Bis-(diphenylphosphino)
Showing ethane. ) is condensed by a Grignard reaction using a nickel-phosphine complex represented by 4 as a catalyst.
．． A 4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound is obtained. Since this production method uses a trans isomer obtained by a known method as a raw material, the product is a trans-trans isomer, and separation and purification of isomers after completion of the reaction is not necessary. Furthermore, since there is no hydrogenation operation, it is safe and the process can be shortened.
以下実施例により本発明の態様を詳しく説明する。Embodiments of the present invention will be explained in detail with reference to Examples below.
実施例 テトラヒドロフラン２５ｔｒＬｔ中のマグネシ
ウム層ｎ２５ｆにＰ−（トランス−４−ｎ−ペンチルシ
クロヘキシル）−ブロムベンゼン五６８Ｖのテトラヒド
ロフラン２５ ｍ ｔの溶液を室温で滴下し、グリニヤ
ール試薬をつくる。これをＰ −（トランス−４−ｎ−
ペンチルシクロヘキシル）−ブロムベンゼン＆３８ｖと
ビス−（トリフェニルホスフィン）ニッケル（ＩＩ）ク
ロライド１．４４ｍｔをテトラヒドロフラン２５ ｇｎ
ｌに溶解した溶液に室温で滴下し、滴下終了後５０時間
還流する。次に反応液を塩酸水溶液中に投じ、クロロホ
ルムにより抽出し、クロロホルム層を水酸化カリウム水
溶液で洗浄する。クロロホルムを留去した後、クロロホ
ルムーアセトンｍ合ｓｓよＩＩ）４ 、４’〜ビス−（
トランス−４−ｎ−ヘンチルシクロヘキシル）ビフェニ
ルを再結晶させる。収量２．６２ｆ ｍｐ、４２℃
ｏｐ、３０２℃
以 上
代理人 弁理士 最上 務Example A solution of P-(trans-4-n-pentylcyclohexyl)-bromobenzene 568 V in 25 mt of tetrahydrofuran is added dropwise to a magnesium layer n25f in 25trLt of tetrahydrofuran at room temperature to prepare a Grignard reagent. This is P − (trans-4-n-
pentylcyclohexyl)-bromobenzene & 38v and bis-(triphenylphosphine)nickel(II) chloride 1.44mt in tetrahydrofuran 25gn
The solution was added dropwise at room temperature to a solution dissolved in 100 ml of water and refluxed for 50 hours after the dropwise addition was completed. Next, the reaction solution is poured into an aqueous hydrochloric acid solution, extracted with chloroform, and the chloroform layer is washed with an aqueous potassium hydroxide solution. After distilling off the chloroform, chloroform acetone m ss II) 4,4'~bis-(
Recrystallize trans-4-n-hentylcyclohexyl)biphenyl. Yield 2.62f mp, 42℃
OP, 302℃ or above Agent Patent Attorney Mogami
Claims (1)
０個の直鎖アルキル基を示す。）で表わされるＰ−（）
ランス−４−アルキルシクロヘキシル）−ブロムベンゼ
ンと、一般式 Ｒ２−＠ｅ−＠−Ｂｒ （式中Ｒ２は水素または炭素数
１〜１０個の直鎖アルキル基を示す。）で表わされるＰ
−（）ランス−４−アルキルシクロヘキシル）−ブロム
ベンゼンの両者をグリニヤール反応により縮合させるこ
とを特徴とする４、４′−ビス−（トランス−４−アル
キルシクロへキシ“ル）−ビフェニル化合物の製造方法
０ ２、特許請求の範囲第一項において、触媒としてニッケ
ルーホスフィン錯体を用いることを特徴とする４、４′
−ビス−（トランス−４−アルキルシクロへキシル）−
ビフェニル化合物の製造方法。 、[Claims] 1. General formula Rz(HtBr (wherein R1 is hydrogen or has 1 to 1 carbon atoms)
Indicates 0 straight chain alkyl groups. ) expressed as P-()
Lance-4-alkylcyclohexyl)-bromobenzene and P represented by the general formula R2-@e-@-Br (wherein R2 represents hydrogen or a straight-chain alkyl group having 1 to 10 carbon atoms).
- Production of a 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound characterized by condensing both (trans-4-alkylcyclohexyl)-bromobenzene by a Grignard reaction. Method 0 2, Claim 1, characterized in that a nickel-phosphine complex is used as the catalyst 4, 4'
-bis-(trans-4-alkylcyclohexyl)-
A method for producing a biphenyl compound. ,
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57091048A JPS58208241A (en) | 1982-05-28 | 1982-05-28 | Preparation of 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57091048A JPS58208241A (en) | 1982-05-28 | 1982-05-28 | Preparation of 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58208241A true JPS58208241A (en) | 1983-12-03 |
Family
ID=14015613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57091048A Pending JPS58208241A (en) | 1982-05-28 | 1982-05-28 | Preparation of 4,4'-bis-(trans-4-alkylcyclohexyl)-biphenyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58208241A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56103120A (en) * | 1979-12-05 | 1981-08-18 | Merck Patent Gmbh | Partially hydrogenated oligoo1*44phenylene compounds and dielectric body and electrooptical display element containing them |
-
1982
- 1982-05-28 JP JP57091048A patent/JPS58208241A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56103120A (en) * | 1979-12-05 | 1981-08-18 | Merck Patent Gmbh | Partially hydrogenated oligoo1*44phenylene compounds and dielectric body and electrooptical display element containing them |
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