JPH0466221B2 - - Google Patents
Info
- Publication number
- JPH0466221B2 JPH0466221B2 JP17413784A JP17413784A JPH0466221B2 JP H0466221 B2 JPH0466221 B2 JP H0466221B2 JP 17413784 A JP17413784 A JP 17413784A JP 17413784 A JP17413784 A JP 17413784A JP H0466221 B2 JPH0466221 B2 JP H0466221B2
- Authority
- JP
- Japan
- Prior art keywords
- chloroformate
- reaction
- carbonate
- producing
- chloroethyl
- 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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- -1 4-methylcyclohexyl Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- IWVJLGPDBXCTDA-UHFFFAOYSA-N cyclohexyl carbonochloridate Chemical compound ClC(=O)OC1CCCCC1 IWVJLGPDBXCTDA-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- ONZWFHWHTYZZLM-UHFFFAOYSA-N 1-chloroethyl cyclohexyl carbonate Chemical compound CC(Cl)OC(=O)OC1CCCCC1 ONZWFHWHTYZZLM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HWRKOBTYLLJBDB-UHFFFAOYSA-N (4-methylcyclohexyl) carbonochloridate Chemical compound CC1CCC(OC(Cl)=O)CC1 HWRKOBTYLLJBDB-UHFFFAOYSA-N 0.000 description 1
- YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 1
- SEEYHRCMNMPHDG-UHFFFAOYSA-N 2-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OCCCl SEEYHRCMNMPHDG-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- DARWLDOSIAZDME-UHFFFAOYSA-N 3-chlorobutan-2-yl hydrogen carbonate Chemical compound CC(Cl)C(C)OC(O)=O DARWLDOSIAZDME-UHFFFAOYSA-N 0.000 description 1
- CANZBRDGRHNSGZ-UHFFFAOYSA-N 3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)C(C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-UHFFFAOYSA-N 0.000 description 1
- PHYMAVMHBUVBON-UHFFFAOYSA-N [1-(1-chloroethyl)cyclopentyl] hydrogen carbonate Chemical compound CC(C1(CCCC1)OC(=O)O)Cl PHYMAVMHBUVBON-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DOSVNAJYHYHGJA-UHFFFAOYSA-N cycloheptyl carbonochloridate Chemical compound ClC(=O)OC1CCCCCC1 DOSVNAJYHYHGJA-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZFQCRLNKHHXELH-UHFFFAOYSA-N cyclopentyl carbonochloridate Chemical compound ClC(=O)OC1CCCC1 ZFQCRLNKHHXELH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17413784A JPS6153243A (ja) | 1984-08-23 | 1984-08-23 | α−クロロエチルシクロアルキルカルボナ−ト類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17413784A JPS6153243A (ja) | 1984-08-23 | 1984-08-23 | α−クロロエチルシクロアルキルカルボナ−ト類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6153243A JPS6153243A (ja) | 1986-03-17 |
| JPH0466221B2 true JPH0466221B2 (fi) | 1992-10-22 |
Family
ID=15973307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17413784A Granted JPS6153243A (ja) | 1984-08-23 | 1984-08-23 | α−クロロエチルシクロアルキルカルボナ−ト類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6153243A (fi) |
-
1984
- 1984-08-23 JP JP17413784A patent/JPS6153243A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6153243A (ja) | 1986-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0745437B2 (ja) | エステルの製造法 | |
| EP0372635B1 (en) | Method of preparing dialkyl and diallyl dicarbonates | |
| EP0147472B1 (en) | 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one | |
| JPS61249964A (ja) | ３，４，５，６−テトラクロロ−２−トリクロロメチルピリジンに富む混合物の調製方法 | |
| EP0108547B1 (en) | Process for the preparation of the 1'-ethoxycarbonyloxyethyl ester of benzylpenicillin | |
| JPH06509553A (ja) | 置換酸のフェニルエステルの製造方法 | |
| JPH0466221B2 (fi) | ||
| WO2004005241A1 (en) | Process for producing optically active amide | |
| JP3164284B2 (ja) | ２−クロロ−４−トリフルオロメチルベンザルクロライドの製造方法 | |
| JP3007610B2 (ja) | シアノホルメートエステルの製造方法 | |
| JP3626520B2 (ja) | ３−置換−３−メチルブタナールの製造方法 | |
| JP4423494B2 (ja) | ２−ヒドロキシカルボン酸の製造法 | |
| JPH0466222B2 (fi) | ||
| JPH0456819B2 (fi) | ||
| JPS60252449A (ja) | α−クロロエチルアルキルカ−ボネ−ト類の製造方法 | |
| JP3163148B2 (ja) | ヘミケタールおよびヘミチオケタールの製造方法 | |
| EP0225778A1 (en) | Improved synthesis and purification of alpha-d-propoxyphene hydrochloride | |
| DD275453A5 (de) | Verfahren zur herstellung von anilinfumarat | |
| US4966993A (en) | Process for preparation of 3-hydroxy-3-methyl-glutaric acid | |
| JPS6239544A (ja) | マロン酸ジエステルの製造法 | |
| JP2006524247A5 (fi) | ||
| JPH11246542A (ja) | 新規なジクロロフタリド及びその製造方法、並びにこれを用いた２−ホルミル安息香酸核塩素化物類の製造方法 | |
| JPS6143144A (ja) | １−クロロアルキルカルボナ−ト類の製造方法 | |
| JP3312414B2 (ja) | ジエン酸ハライド類の製造方法 | |
| JPH06145107A (ja) | β−ケトカルボン酸エステルの製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |