DE3325976A1 - Verfahren zur herstellung von 4-homoisotwistan-3-carbonsaeure - Google Patents
Verfahren zur herstellung von 4-homoisotwistan-3-carbonsaeureInfo
- Publication number
- DE3325976A1 DE3325976A1 DE19833325976 DE3325976A DE3325976A1 DE 3325976 A1 DE3325976 A1 DE 3325976A1 DE 19833325976 DE19833325976 DE 19833325976 DE 3325976 A DE3325976 A DE 3325976A DE 3325976 A1 DE3325976 A1 DE 3325976A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reaction
- inorganic
- strongly acidic
- acidic catalyst
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 claims description 2
- LKWKIVHUCKVYOA-UHFFFAOYSA-N phosphoric acid;trifluoroborane Chemical compound FB(F)F.OP(O)(O)=O LKWKIVHUCKVYOA-UHFFFAOYSA-N 0.000 claims description 2
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JPWBFRWFHBFLJX-UHFFFAOYSA-N decan-3-yl acetate Chemical compound CCCCCCCC(CC)OC(C)=O JPWBFRWFHBFLJX-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 3
- 238000006473 carboxylation reaction Methods 0.000 description 3
- -1 formyloxymethyl group Chemical group 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- MCEWXTWROUCMOU-UHFFFAOYSA-N decahydro-1,6-methanonaphthalene Chemical group C1CC2C3CCCC2CC1C3 MCEWXTWROUCMOU-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
- C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
- C07C61/135—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57128234A JPS5920244A (ja) | 1982-07-22 | 1982-07-22 | ４−ホモイソツイスタン−３−カルボン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3325976A1 true DE3325976A1 (de) | 1984-01-26 |
| DE3325976C2 DE3325976C2 (en, 2012) | 1991-11-07 |
Family
ID=14979804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833325976 Granted DE3325976A1 (de) | 1982-07-22 | 1983-07-19 | Verfahren zur herstellung von 4-homoisotwistan-3-carbonsaeure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4585893A (en, 2012) |
| JP (1) | JPS5920244A (en, 2012) |
| CH (1) | CH654290A5 (en, 2012) |
| DE (1) | DE3325976A1 (en, 2012) |
| FR (1) | FR2530622B1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541212B2 (en) | 1997-03-10 | 2003-04-01 | The Regents Of The University Of California | Methods for detecting prostate stem cell antigen protein |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111752A (en) * | 1974-07-16 | 1976-01-30 | Kao Corp | 44 homoisotsuisutankarubonsanno seiho |
| JPS5111751A (en) * | 1974-07-16 | 1976-01-30 | Kao Corp | 44 homoisotsuisuchirukarubinooruno seizoho |
| JPS523046A (en) * | 1975-06-24 | 1977-01-11 | Kao Corp | Prepration of 4-homotwistane-3-carboxylic acid esters |
| JPS5273847A (en) * | 1975-12-15 | 1977-06-21 | Kao Corp | Preparation of 4-homoisotwistane-3-carboxylic acid |
-
1982
- 1982-07-22 JP JP57128234A patent/JPS5920244A/ja active Granted
-
1983
- 1983-07-18 US US06/514,847 patent/US4585893A/en not_active Expired - Lifetime
- 1983-07-19 DE DE19833325976 patent/DE3325976A1/de active Granted
- 1983-07-20 CH CH3976/83A patent/CH654290A5/de not_active IP Right Cessation
- 1983-07-22 FR FR8312134A patent/FR2530622B1/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Chem. Abstr. 87, 1977, 167624g * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2530622A1 (fr) | 1984-01-27 |
| DE3325976C2 (en, 2012) | 1991-11-07 |
| JPH0226617B2 (en, 2012) | 1990-06-12 |
| CH654290A5 (de) | 1986-02-14 |
| FR2530622B1 (fr) | 1986-05-02 |
| US4585893A (en) | 1986-04-29 |
| JPS5920244A (ja) | 1984-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1695753C3 (de) | Verfahren zur Herstellung von 6,6disubstituierten 2,2-Dimethyl-4-oxopiperidinen | |
| DE2431242C3 (de) | 2,7,10,15,18,23-Hexamethyltetracosan und Verfahren zu seiner Herstellung | |
| DE2413178B2 (de) | Verfahren zur Herstellung von 12-Aminododecansäureestern | |
| DE1964763A1 (de) | Verfahren zur Herstellung von Halogenkohlenwasserstoffen | |
| DE3325983C2 (en, 2012) | ||
| DE2630981C2 (de) | 4-β,β-Dichlor- und 4-β,β-Dibromvinyl-3,3-dimethylbutyrolactone, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Estern der 3-β,β-Dichlor- oder 3-β,β-Dibrom-vinyl-2,2-dimethylcyclopropancarbonsäure | |
| EP0089417B1 (de) | Verfahren zur Herstellung von Phthalid | |
| DE3325976C2 (en, 2012) | ||
| CH495944A (de) | Verfahren zur Herstellung von a-Methyl-polycyclomethylaminen | |
| DE2558399C3 (de) | Verfahren zur Herstellung von 3,6-Dichlorpicolinsäure | |
| DE69606389T2 (de) | Tricyclocarboxylate, verfahren zur herstellung sowie darauf basierendes parfum | |
| DE2202249C2 (de) | Verfahren zur Gewinnung von α-Cedren aus der Kohlenwasserstoffraktion von Zedernholzöl | |
| DE2703640A1 (de) | Verfahren zur herstellung von aromatischen methylendioxy-verbindungen | |
| DE3437634A1 (de) | Verfahren zur herstellung von gegebenenfalls substituierter zimtsaeure in gegenwart eines katalysators | |
| DE2135666A1 (de) | Verfahren zur herstellung von cycloalkylidenacetonitrilen | |
| DE1960941A1 (de) | Verfahren zur Herstellung von Methylcyclohexenen | |
| DE2703077A1 (de) | Verfahren zur herstellung von cyclohexandion-(1,4)-tetramethyl- diketal | |
| EP0583752A1 (de) | Verfahren zur Herstellung von 1,2:5,6-Di-O-isopropyliden derivaten von Monosacchariden, insbesondere von 1,2-5,6-Diaceton-D-glucose | |
| EP0561213A1 (de) | Verfahren zur Herstellung von Hydroxypivalinsäureneopentylglykolester | |
| DE2120248A1 (en, 2012) | ||
| DE1668280B2 (de) | Verfahren zur herstellung von dihydromyrcenol | |
| DE4416661A1 (de) | Propylenglykol-Monomethyletherbutyrate und deren Isomere sowie Verfahren zur Herstellung derselben | |
| DE2042050C (de) | Verfahren zur Herstellung von 1-Menthylmethylcarbonat bzw. 1-Menthyläthylcarbonat | |
| DE2233489C3 (de) | Verfahren zur Herstellung von Octachlordipropyläther | |
| AT215420B (de) | Verfahren zur Herstellung von 1-Methyl-3-pyrrolidyl-methylalkohol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |