JPH04975B2 - - Google Patents
Info
- Publication number
- JPH04975B2 JPH04975B2 JP9728483A JP9728483A JPH04975B2 JP H04975 B2 JPH04975 B2 JP H04975B2 JP 9728483 A JP9728483 A JP 9728483A JP 9728483 A JP9728483 A JP 9728483A JP H04975 B2 JPH04975 B2 JP H04975B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- cyano
- trans
- liquid crystal
- formula
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 48
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 pentylcyclohexyl Chemical group 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- FRHMUQJTUZKWML-UHFFFAOYSA-N 4-[2-(4-pentylphenyl)phenyl]benzoic acid Chemical compound C(CCCC)C1=CC=C(C=C1)C=1C(=CC=CC1)C1=CC=C(C=C1)C(=O)O FRHMUQJTUZKWML-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XWQDMIXVAYAZGB-UHFFFAOYSA-N 5-chloro-2-hydroxybenzonitrile Chemical compound OC1=CC=C(Cl)C=C1C#N XWQDMIXVAYAZGB-UHFFFAOYSA-N 0.000 description 3
- MWLKQSIMPLORKX-UHFFFAOYSA-N 5-fluoro-2-hydroxybenzonitrile Chemical compound OC1=CC=C(F)C=C1C#N MWLKQSIMPLORKX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BTOPYVYSWZMILE-VNRTZBFSSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(=O)OC=2C(=CC(F)=CC=2)C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(=O)OC=2C(=CC(F)=CC=2)C#N)C=C1 BTOPYVYSWZMILE-VNRTZBFSSA-N 0.000 description 3
- GLVQBAYHWDUEQI-YKFMMLSNSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 GLVQBAYHWDUEQI-YKFMMLSNSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- PXWQEKIHOLLUCD-VNRTZBFSSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(=O)OC=2C(=CC(Cl)=CC=2)C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(=O)OC=2C(=CC(Cl)=CC=2)C#N)C=C1 PXWQEKIHOLLUCD-VNRTZBFSSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9728483A JPS59222464A (ja) | 1983-06-01 | 1983-06-01 | ２−シアノ−４−ハロゲノフエノ−ルのエステル類 |
| US06/530,786 US4603018A (en) | 1982-09-27 | 1983-09-09 | 2-cyano-4-halogenophenyl esters |
| EP83305765A EP0106588B1 (en) | 1982-09-27 | 1983-09-27 | 2-cyano-4-halogenophenyl esters |
| DE8383305765T DE3363290D1 (de) | 1982-09-27 | 1983-09-27 | 2-cyano-4-halogenophenyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9728483A JPS59222464A (ja) | 1983-06-01 | 1983-06-01 | ２−シアノ−４−ハロゲノフエノ−ルのエステル類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59222464A JPS59222464A (ja) | 1984-12-14 |
| JPH04975B2 true JPH04975B2 (en]) | 1992-01-09 |
Family
ID=14188209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9728483A Granted JPS59222464A (ja) | 1982-09-27 | 1983-06-01 | ２−シアノ−４−ハロゲノフエノ−ルのエステル類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59222464A (en]) |
-
1983
- 1983-06-01 JP JP9728483A patent/JPS59222464A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59222464A (ja) | 1984-12-14 |
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