JPS6251259B2 - - Google Patents
Info
- Publication number
- JPS6251259B2 JPS6251259B2 JP6498880A JP6498880A JPS6251259B2 JP S6251259 B2 JPS6251259 B2 JP S6251259B2 JP 6498880 A JP6498880 A JP 6498880A JP 6498880 A JP6498880 A JP 6498880A JP S6251259 B2 JPS6251259 B2 JP S6251259B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- acid
- compound
- mol
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000004973 liquid crystal related substance Substances 0.000 claims description 22
- -1 phenyl ester Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 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 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FNUWTRXUMODLEK-UHFFFAOYSA-N 1-(bromomethyl)-4-propylcyclohexane Chemical compound CCCC1CCC(CBr)CC1 FNUWTRXUMODLEK-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AGBINQHSDMZNBI-MGCOHNPYSA-N CCC[C@H]1CC[C@H](CO)CC1 Chemical compound CCC[C@H]1CC[C@H](CO)CC1 AGBINQHSDMZNBI-MGCOHNPYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6498880A JPS56161352A (en) | 1980-05-16 | 1980-05-16 | 4"-substituted phenyl 4-(4-trans-4'-alkylcyclohexylmethoxy)benzoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6498880A JPS56161352A (en) | 1980-05-16 | 1980-05-16 | 4"-substituted phenyl 4-(4-trans-4'-alkylcyclohexylmethoxy)benzoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56161352A JPS56161352A (en) | 1981-12-11 |
| JPS6251259B2 true JPS6251259B2 (en, 2012) | 1987-10-29 |
Family
ID=13273933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6498880A Granted JPS56161352A (en) | 1980-05-16 | 1980-05-16 | 4"-substituted phenyl 4-(4-trans-4'-alkylcyclohexylmethoxy)benzoate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56161352A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4314883A1 (de) * | 1993-05-05 | 1994-11-10 | Trw Repa Gmbh | Sicherheitsgurtaufroller |
-
1980
- 1980-05-16 JP JP6498880A patent/JPS56161352A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56161352A (en) | 1981-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4330426A (en) | Cyclohexylbiphenyls, their preparation and use in dielectrics and electrooptical display elements | |
| EP0407438B1 (en) | Laterally fluorinated 4-cyanophenyl and 4'-cyanobiphenyl benzoates | |
| JPS6338342B2 (en, 2012) | ||
| JPS6358815B2 (en, 2012) | ||
| EP0272580B1 (en) | Liquidcrystalline cyclohexylbenzene derivatives their manufacturing and novel nematic admixtures containing same | |
| JP2746711B2 (ja) | フッ素化４″― シアノ置換ターフェニル | |
| JPS632246B2 (en, 2012) | ||
| JPS6346740B2 (en, 2012) | ||
| JPS63310838A (ja) | トラン型新規液晶化合物 | |
| JPS643858B2 (en, 2012) | ||
| JPS6251259B2 (en, 2012) | ||
| JPS60209539A (ja) | ネマチツク液晶化合物並びに液晶組成物 | |
| JPS6183190A (ja) | ２−（４′−置換フエニル）−５−アルキル−１，３，２−ジオキサボリナン化合物，その製造法及びそれを含有する液晶組成物 | |
| US5312563A (en) | Fluorinated 4"-cyano substituted terphenyls | |
| JPH04502627A (ja) | フェニルシクロヘキサン化合物および液晶相 | |
| JPS6321658B2 (en, 2012) | ||
| JPH0131500B2 (en, 2012) | ||
| JPS59110631A (ja) | １，４−ジ−（シクロヘキシルエチル）ビフエニル誘導体 | |
| JP2829436B2 (ja) | シクロブタン誘導体 | |
| JPS59193848A (ja) | 新規ネマチツク液晶化合物 | |
| JPS6346742B2 (en, 2012) | ||
| JP2500687B2 (ja) | ビシクロヘキシルトラン誘導体 | |
| JPH0335302B2 (en, 2012) | ||
| JP4094742B2 (ja) | エステル化合物ならびにそれを含有する液晶組成物 | |
| JPS6059223B2 (ja) | 液晶性化合物 |