JPH0118914B2 - - Google Patents
Info
- Publication number
- JPH0118914B2 JPH0118914B2 JP6419381A JP6419381A JPH0118914B2 JP H0118914 B2 JPH0118914 B2 JP H0118914B2 JP 6419381 A JP6419381 A JP 6419381A JP 6419381 A JP6419381 A JP 6419381A JP H0118914 B2 JPH0118914 B2 JP H0118914B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- tris
- trifluoromethylethyl
- trioxane
- yield
- 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
- 239000007983 Tris buffer Substances 0.000 claims description 16
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QLHMHPBDSYKXRI-UHFFFAOYSA-N 3,3,3-trifluoro-2-methylpropanal Chemical compound O=CC(C)C(F)(F)F QLHMHPBDSYKXRI-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- XFGVJLGVINCWDP-UHFFFAOYSA-N 5,5,5-trifluoroleucine Chemical compound FC(F)(F)C(C)CC(N)C(O)=O XFGVJLGVINCWDP-UHFFFAOYSA-N 0.000 description 4
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- -1 2-oximino-4-trifluoromethylvaleric acid Chemical compound 0.000 description 2
- FFZMMBKGTNDVRX-UHFFFAOYSA-N 4,4,4-trifluoro-3-methylbutanoic acid Chemical compound FC(F)(F)C(C)CC(O)=O FFZMMBKGTNDVRX-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- QRRCTLYMABZQCS-IHWYPQMZSA-N (z)-4,4,4-trifluoro-3-methylbut-2-enoic acid Chemical compound FC(F)(F)C(/C)=C\C(O)=O QRRCTLYMABZQCS-IHWYPQMZSA-N 0.000 description 1
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- FGSQNGXPFOBJRZ-UHFFFAOYSA-N 3-fluoro-2-methylpropanal Chemical compound FCC(C)C=O FGSQNGXPFOBJRZ-UHFFFAOYSA-N 0.000 description 1
- JCJGOWYCFRASTM-UHFFFAOYSA-N 4,4,4-trifluoro-3-hydroxy-3-methylbutanoic acid Chemical compound FC(F)(F)C(O)(C)CC(O)=O JCJGOWYCFRASTM-UHFFFAOYSA-N 0.000 description 1
- KDEWPMLKHLACHF-UHFFFAOYSA-N 5,5,5-trifluoro-4-methyl-2-oxopentanoic acid Chemical compound FC(F)(F)C(C)CC(=O)C(O)=O KDEWPMLKHLACHF-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000004716 alpha keto acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SRVTXLPAWBTQSA-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-methylbutanoate Chemical compound CCOC(=O)CC(C)C(F)(F)F SRVTXLPAWBTQSA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FTHUKEBATJXQFL-UHFFFAOYSA-N formic acid;hydrochloride Chemical compound Cl.OC=O FTHUKEBATJXQFL-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6419381A JPS57181078A (en) | 1981-04-30 | 1981-04-30 | 2,4,6-tris(1-trifluoromethylethyl)trioxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6419381A JPS57181078A (en) | 1981-04-30 | 1981-04-30 | 2,4,6-tris(1-trifluoromethylethyl)trioxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57181078A JPS57181078A (en) | 1982-11-08 |
| JPH0118914B2 true JPH0118914B2 (enrdf_load_stackoverflow) | 1989-04-07 |
Family
ID=13250979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6419381A Granted JPS57181078A (en) | 1981-04-30 | 1981-04-30 | 2,4,6-tris(1-trifluoromethylethyl)trioxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57181078A (enrdf_load_stackoverflow) |
-
1981
- 1981-04-30 JP JP6419381A patent/JPS57181078A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57181078A (en) | 1982-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0133456B2 (enrdf_load_stackoverflow) | ||
| CA1331185C (en) | Intermediates for preparing 1,4-dihydro-4-oxo- quinoline-3-carboxylic acid esters | |
| JPH0118914B2 (enrdf_load_stackoverflow) | ||
| Hua et al. | Preparation of (S)-(-)-4-methyl-2-cyclohexen-1-one. A useful chiral building block | |
| DE2533387C2 (de) | Verfahren zur Herstellung von 2-Hydroxy-3-butensäureestern | |
| JPH0662488B2 (ja) | バルプロ酸の製造方法 | |
| DE2533335C2 (de) | 3-Methyl-3-aryl-brenztraubensäureester und Verfahren zur Herstellung substituierter Brenztraubensäureester | |
| US2098206A (en) | Manufacture of alcohols | |
| JPH0537140B2 (enrdf_load_stackoverflow) | ||
| JPS6353980B2 (enrdf_load_stackoverflow) | ||
| JPH0193554A (ja) | 有機化合物 | |
| JPS625411B2 (enrdf_load_stackoverflow) | ||
| JP3203082B2 (ja) | 分岐脂肪酸の製造法 | |
| JPS59112941A (ja) | ３−メチル−４−ペンテン−１−オ−ル誘導体の製造方法 | |
| Nakano et al. | SYNTHESIS OF CHLOROALKANE-α, ω-DIOIC ACIDS | |
| JPS6136742B2 (enrdf_load_stackoverflow) | ||
| JPH05132445A (ja) | フルオロアルカン酸及びその製造方法 | |
| JP2003113189A (ja) | シクロペンタベンゾフラン誘導体の製造方法及びその製造原料となる新規化合物 | |
| JP2001048826A (ja) | １−フェニル−１，３−ブタンジオン誘導体の製造方法 | |
| WO1998016495A1 (fr) | Processus de preparation de monoesters d'acide dicarboxylique | |
| JP3635118B2 (ja) | プロパルギルフリルメチルアルコールの製造方法 | |
| JP3047338B2 (ja) | α−メルカプトフロロアルキルカルボン酸と２−メルカプトフロロアルキルアルコールおよびそれらの製造方法 | |
| JP2853929B2 (ja) | ２−クロロ−４，５−ジフルオロ−３−メトキシ安息香酸の製造方法 | |
| JP2603869B2 (ja) | ３‐オキソ‐５‐ヘキセン酸エステル類の製造法 | |
| JPH0791216B2 (ja) | α−（３−（１−フエニルエチル）フェニル）プロピオン酸 |