JPH0219344A - 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester and production thereof - Google Patents
4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester and production thereofInfo
- Publication number
- JPH0219344A JPH0219344A JP63168929A JP16892988A JPH0219344A JP H0219344 A JPH0219344 A JP H0219344A JP 63168929 A JP63168929 A JP 63168929A JP 16892988 A JP16892988 A JP 16892988A JP H0219344 A JPH0219344 A JP H0219344A
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- formula
- halogenophenyl
- cyclohexanecarboxylic acid
- trans
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 3-cyclohexenecarboxylic acid ester Chemical class 0.000 claims abstract description 7
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ROHLQNZWNPRZDC-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C1=CC=C(Cl)C=C1 ROHLQNZWNPRZDC-UHFFFAOYSA-N 0.000 description 1
- IPUNVLFESXFVFH-UHFFFAOYSA-N methyl cyclohex-3-ene-1-carboxylate Chemical compound COC(=O)C1CCC=CC1 IPUNVLFESXFVFH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、液晶や医農薬等の重要な中間体である４−（
４’−ハロゲノフェニル）−シクロヘキサンカルボン酸
エステル及びその製造方法に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to 4-(
The present invention relates to 4'-halogenophenyl)-cyclohexanecarboxylic acid ester and a method for producing the same.
［従来の技術及びその課題］
近年液晶デイスプレィ利用分野の拡大に伴いより広範囲
に利用でき、高品位で低価格の液晶が求められており、
安価で応用範囲の広い液晶原料の供給が要望されている
。一方、医農薬中間体等においても、応用範囲が広（し
かも安価で容易に製造できる原料を提供することは重要
な課題となっている。[Conventional technology and its issues] As the field of use of liquid crystal displays has expanded in recent years, there has been a demand for high-quality, low-cost liquid crystals that can be used more widely.
There is a demand for the supply of liquid crystal raw materials that are inexpensive and have a wide range of applications. On the other hand, in the field of pharmaceutical and agricultural intermediates, etc., it is an important issue to provide raw materials that have a wide range of application (and can be produced easily at low cost).
［課題を解決するための手段］
本発明は、前述の課題を解決すべくなされたものであり
、下記一般式（Ｉ）で表わされる４−（４’−ハロゲノ
フェニル）−シクロヘキサンカルボン酸エステル及びそ
の製造方法を提供するものである。[Means for Solving the Problems] The present invention has been made to solve the above-mentioned problems, and includes a 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester represented by the following general formula (I) and The present invention provides a method for manufacturing the same.
（式中、Ｘはハロゲン原子、Ｒは炭素は１〜５のアルキ
ル基を示す。）
式中Ｘは、塩素原子、フッ素原子、臭素原子又はシス−
１，４ジ置換シクロヘキサン環を示し、トランス体が液
晶や医農薬等の中間体として重要である。Ｒは炭素数１
〜５のアルキル基であり、特にメチル基が好ましい。(In the formula, X is a halogen atom, R is an alkyl group having 1 to 5 carbon atoms.) In the formula, X is a chlorine atom, a fluorine atom, a bromine atom, or
It represents a 1,4-disubstituted cyclohexane ring, and the trans isomer is important as an intermediate for liquid crystals, medicines and agricultural chemicals, etc. R is carbon number 1
-5 alkyl group, with methyl group being particularly preferred.
前記一般式（Ｉ）で表わされる化合物の製造方法として
は、モノハロゲノベンゼンと３−シクロヘキセンカルボ
ン酸エステルとをルイス酸触媒の存在下に反応させる方
法が好ましい。反応シス又はシス−１，４ジ置換シクロ
ヘキサン環となる混合物である。A preferred method for producing the compound represented by the general formula (I) is a method in which monohalogenobenzene and 3-cyclohexenecarboxylic acid ester are reacted in the presence of a Lewis acid catalyst. It is a mixture that results in a reactive cis- or cis-1,4-disubstituted cyclohexane ring.
ルイス酸触媒としては、ＡｌＣｌ５ ＋ ＡｌＢｒ３＊
ＺｎＣ１ｚ 、 ＢＦ３ 、 ＢＣｌ３ 、 ＢＢｒ３
． ＴｉＣｌ４． ＦｅＣ：１３等周期律表■〜Ｖ族、
■族の広範囲にわたる原子のハロゲン化物でよいが、特
に性能も良く安価であることから、ＡＩＣ：Ｉｓが好ま
しい。無溶媒でもよいが、反応溶媒としては、ジクロル
エタン、塩化メチレン、フルオロトリクロロメタン、１
４．２−トリクロロトリフルオロエタン等のハロゲン化
炭化水素類又は、これらの混合物等、反応に不活性な溶
媒を使用すればよい。反応温度は一１０℃〜４０℃、好
ましくは１５℃〜２５℃であり、反応圧力は常圧又は加
圧下に実施すればよい。As a Lewis acid catalyst, AlCl5 + AlBr3*
ZnC1z, BF3, BCl3, BBr3
．． TiCl4. FeC: 13th grade periodic table ■~V group,
Halides of a wide range of atoms in group (2) may be used, but AIC:Is is preferred because it has particularly good performance and is inexpensive. Although no solvent may be used, examples of reaction solvents include dichloroethane, methylene chloride, fluorotrichloromethane, 1
A solvent inert to the reaction may be used, such as halogenated hydrocarbons such as 4.2-trichlorotrifluoroethane or a mixture thereof. The reaction temperature is -10°C to 40°C, preferably 15°C to 25°C, and the reaction pressure may be normal pressure or increased pressure.
モノハロゲノベンゼンと３−シクロヘキセンカルボン酸
エステルとの反応モル比は、１：１〜１０：１．好まし
くは２：１〜４：１が適当である。ルイス酸触媒の存在
量は、３−シクロヘキセンカルボン酸エステル１モルに
対して０．５〜２．０モル、好ましくは１−１．５モル
の範囲から選定すればよい。The reaction molar ratio of monohalogenobenzene and 3-cyclohexenecarboxylic acid ester is 1:1 to 10:1. Preferably, a ratio of 2:1 to 4:1 is appropriate. The amount of Lewis acid catalyst present may be selected from the range of 0.5 to 2.0 mol, preferably 1 to 1.5 mol, per 1 mol of 3-cyclohexenecarboxylic acid ester.
モノハロゲノベンゼンは、クロルベンゼン、フルオロベ
ンゼン、ブロモベンゼン等であり、３−シクロヘキセン
カルボン酸エステルは、炭素数１〜５のアルキルエステ
ルであり、これらはいずれも工業的に入手容易な安価な
化合物である。Monohalogenobenzene is chlorobenzene, fluorobenzene, bromobenzene, etc., and 3-cyclohexenecarboxylic acid ester is an alkyl ester having 1 to 5 carbon atoms, and all of these are inexpensive compounds that are easily available industrially. be.
本発明の４−（４’−ハロゲノフェニル）−シクロヘキ
サンカルボン酸エステルは、カルボキシル基やハロゲン
原子を反応に関与させることにより、多方面にわたる機
能製品の製造が可能である。例えば、特開昭６０−８４
２３０号に記載された液晶物質として有用なｌ−トラン
ス−４′−（トランス−４″−アルキルシクロヘキシル
）シクロへキシル−２−（４”’−置換フェニル）エタ
ンの原料とすることができる。The 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester of the present invention can be used to produce a wide variety of functional products by involving a carboxyl group or a halogen atom in the reaction. For example, JP-A-60-84
It can be used as a raw material for l-trans-4'-(trans-4''-alkylcyclohexyl)cyclohexyl-2-(4''-substituted phenyl)ethane, which is useful as a liquid crystal material described in No. 230.
［実施例］
以下、実施例により、本発明の製造方法を更に詳しく説
明する。[Example] Hereinafter, the manufacturing method of the present invention will be explained in more detail with reference to Examples.
実施例１
クロルベンゼン１１２．６ｇ（１，０モル）と無水塩化
アルミニウム６０ｇ（０，４５モル）とを３００＋ｏ１
２四ツロフラスコ中に混合、攪拌下に３−シクロヘキセ
ンカルボン酸メチル４２ｇ（０，３モル）を滴下ロート
より２０℃、１時間を要して滴下する。その後室温で１
２時間反応し、反応液を氷水中に注ぎ分解する。油層を
分液、水層をｎ−ヘキサンで抽出し合せて水洗浄する。Example 1 112.6 g (1.0 mol) of chlorobenzene and 60 g (0.45 mol) of anhydrous aluminum chloride were mixed at 300+o1
42 g (0.3 mol) of methyl 3-cyclohexenecarboxylate was added dropwise to the flask at 20 DEG C. over 1 hour while mixing and stirring. Then at room temperature 1
After reacting for 2 hours, the reaction solution was poured into ice water and decomposed. The oil layer is separated and the aqueous layer is extracted with n-hexane and washed with water.
溶媒を留去した粗油を減圧下に蒸留し、４−（４−クロ
ルフェニル）−シクロヘキサンカルボン酸メチルのシス
、トランス混合物６１ｇを得た。メタノールから再結晶
し、トランス体２０．５ｇを得た。収率２７％、融点６
８．５℃、このトランス体のＩＲスペクトルを第１図に
示す。The crude oil from which the solvent was distilled off was distilled under reduced pressure to obtain 61 g of a cis-trans mixture of methyl 4-(4-chlorophenyl)-cyclohexanecarboxylate. Recrystallization from methanol yielded 20.5 g of trans isomer. Yield 27%, melting point 6
The IR spectrum of this trans isomer at 8.5° C. is shown in FIG.
第１図は、トランス−４−（４’−クロルフェニル−（
シクロヘキサンカルボン酸メチルのＩＲスペクトル図で
ある。Figure 1 shows trans-4-(4'-chlorophenyl-(
It is an IR spectrum diagram of methyl cyclohexanecarboxylate.
Claims (1)
ゲノフェニル）−シクロヘキサンカルボン酸エステル ▲数式、化学式、表等があります▼・・・・・（ I ） （式中、Ｘはハロゲン原子、Ｒ炭素は１〜５のアルキル
基を示す。） ２、モノハロゲノベンゼンと３−シクロヘキセンカルボ
ン酸エステルとをルイス酸触媒の存在下に反応させるこ
とを特徴とする４−（４′−ハロゲノフェニル）−シク
ロヘキサンカルボン酸エステルの製造方法。[Claims] 1. 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester represented by the following general formula (I)▲There are numerical formulas, chemical formulas, tables, etc.▼・・・・・・(I) ( (In the formula, X represents a halogen atom, and R carbon represents an alkyl group of 1 to 5.) 2. Monohalogenobenzene and 3-cyclohexenecarboxylic acid ester are reacted in the presence of a Lewis acid catalyst. A method for producing -(4'-halogenophenyl)-cyclohexanecarboxylic acid ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63168929A JPH0219344A (en) | 1988-07-08 | 1988-07-08 | 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63168929A JPH0219344A (en) | 1988-07-08 | 1988-07-08 | 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0219344A true JPH0219344A (en) | 1990-01-23 |
Family
ID=15877167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63168929A Pending JPH0219344A (en) | 1988-07-08 | 1988-07-08 | 4-(4'-halogenophenyl)-cyclohexanecarboxylic acid ester and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0219344A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104628555A (en) * | 2015-01-05 | 2015-05-20 | 烟台蓓丰医药科技有限公司 | Synthesis method of drug intermediate 4-(4-chlorphenyl) cyclohexyl-1-formic acid |
| JP6003643B2 (en) * | 2010-06-10 | 2016-10-05 | 宇部興産株式会社 | Catalyst for alkylation reaction and method for producing alkyl aromatic hydrocarbon compound using the catalyst |
| JP2017002006A (en) * | 2015-06-15 | 2017-01-05 | Dic株式会社 | Manufacturing method of carbonyl compound |
| JP2017002005A (en) * | 2015-06-15 | 2017-01-05 | Dic株式会社 | Manufacturing method of carbonyl compound using decarboxylation reaction |
-
1988
- 1988-07-08 JP JP63168929A patent/JPH0219344A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6003643B2 (en) * | 2010-06-10 | 2016-10-05 | 宇部興産株式会社 | Catalyst for alkylation reaction and method for producing alkyl aromatic hydrocarbon compound using the catalyst |
| CN104628555A (en) * | 2015-01-05 | 2015-05-20 | 烟台蓓丰医药科技有限公司 | Synthesis method of drug intermediate 4-(4-chlorphenyl) cyclohexyl-1-formic acid |
| CN104628555B (en) * | 2015-01-05 | 2016-11-30 | 烟台蓓丰医药科技有限公司 | A kind of synthetic method of pharmaceutical intermediate 4-(4-chlorphenyl) cyclohexyl-1-formic acid |
| JP2017002006A (en) * | 2015-06-15 | 2017-01-05 | Dic株式会社 | Manufacturing method of carbonyl compound |
| JP2017002005A (en) * | 2015-06-15 | 2017-01-05 | Dic株式会社 | Manufacturing method of carbonyl compound using decarboxylation reaction |
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