JPS60126288A - スピロオルソカ−ボネ−トの製造方法 - Google Patents
スピロオルソカ−ボネ−トの製造方法Info
- Publication number
- JPS60126288A JPS60126288A JP58232242A JP23224283A JPS60126288A JP S60126288 A JPS60126288 A JP S60126288A JP 58232242 A JP58232242 A JP 58232242A JP 23224283 A JP23224283 A JP 23224283A JP S60126288 A JPS60126288 A JP S60126288A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- formula
- alkyl group
- norbornene
- 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 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 238000006243 chemical reaction Methods 0.000 abstract description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 10
- 239000007787 solid Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000008096 xylene Substances 0.000 abstract description 5
- -1 orthocarbonic acid ester Chemical class 0.000 abstract description 4
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 abstract description 4
- DSHXMENPUICESR-UHFFFAOYSA-N [5-(hydroxymethyl)-5-bicyclo[2.2.1]hept-2-enyl]methanol Chemical compound C1C2C(CO)(CO)CC1C=C2 DSHXMENPUICESR-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 8
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LFMXSZSVDQJYDU-UHFFFAOYSA-N 1-(tripropoxymethoxy)propane Chemical compound CCCOC(OCCC)(OCCC)OCCC LFMXSZSVDQJYDU-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical compound OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58232242A JPS60126288A (ja) | 1983-12-10 | 1983-12-10 | スピロオルソカ−ボネ−トの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58232242A JPS60126288A (ja) | 1983-12-10 | 1983-12-10 | スピロオルソカ−ボネ−トの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60126288A true JPS60126288A (ja) | 1985-07-05 |
| JPH0545597B2 JPH0545597B2 (enrdf_load_stackoverflow) | 1993-07-09 |
Family
ID=16936195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58232242A Granted JPS60126288A (ja) | 1983-12-10 | 1983-12-10 | スピロオルソカ−ボネ−トの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60126288A (enrdf_load_stackoverflow) |
-
1983
- 1983-12-10 JP JP58232242A patent/JPS60126288A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0545597B2 (enrdf_load_stackoverflow) | 1993-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Reddy et al. | Calixarenes. 32. Reactions of calix [4] quinones | |
| EP0372635B1 (en) | Method of preparing dialkyl and diallyl dicarbonates | |
| JPS5810582A (ja) | スピロオルトカ−ボネ−トの製造法 | |
| JPS60126288A (ja) | スピロオルソカ−ボネ−トの製造方法 | |
| US4870193A (en) | Process for producing spiro-orthocarbonate | |
| US3839387A (en) | Process for preparing n-trimethyl-silylacetamide | |
| JPH0217183A (ja) | 環式硫酸エステル類の製造方法 | |
| JPH069610A (ja) | 置換１，３−ジオキソラン−２−オン誘導体の製法 | |
| US3799940A (en) | Process for producing aromatic aldehydes | |
| KR830002449B1 (ko) | 4-트리클로로 메톡시벤조일 클로라이드의 개선된 제조방법 | |
| Goto et al. | Syntheses and structural characterizations of a novel bowl-type germanol and its derivatives | |
| JPH0796514B2 (ja) | ジヒドロキシベンゼンのモノおよびビス（ヒドロキシエチル）エーテルの製造方法 | |
| JPH0352839A (ja) | ｐ‐又はｍ‐ｔｅｒｔ―ブトキシベンズアルデヒドの製造法 | |
| JP2007001888A (ja) | １，４−ジヒドロ−１，４−メタノアントラセン類の製造方法 | |
| JPS60237039A (ja) | ベンザルアセトフエノン及びその誘導体の製造方法 | |
| JPS5835137A (ja) | ヒドロキシアルキルビニルエ−テルの製造方法 | |
| SU777033A1 (ru) | Способ получени 2-( -хлорэтил)1,3-диоксолана | |
| SU1567565A1 (ru) | Способ получени 1-хлор-4-метилпентан-2-ола | |
| JPS60100582A (ja) | ３，９−ジメチレン−１，５，７，１１−テトラオキサスピロ〔５，５〕ウンデカンの製造方法 | |
| JPH062716B2 (ja) | 芳香族第二級アミノ化合物の製造方法 | |
| JPS6248648A (ja) | ジアルコキシ酢酸エステル化合物の製造法 | |
| JPH05345739A (ja) | ３，４’−ジクロロジフェニルエーテルの製造方法 | |
| JPH04164085A (ja) | スピロオルソカーボネート化合物の製造方法 | |
| US3661743A (en) | Photochemical process for preparing beta-thiolactones | |
| JPS61130258A (ja) | １―ブロモエチルヒドロカルボニルカーボネートの製造方法 |