FI92054C - Menetelmä 3-(o-metoksifenoksi)-1,2-propaanidioli-1-karbamaatin valmistamiseksi - Google Patents
Menetelmä 3-(o-metoksifenoksi)-1,2-propaanidioli-1-karbamaatin valmistamiseksi Download PDFInfo
- Publication number
- FI92054C FI92054C FI891068A FI891068A FI92054C FI 92054 C FI92054 C FI 92054C FI 891068 A FI891068 A FI 891068A FI 891068 A FI891068 A FI 891068A FI 92054 C FI92054 C FI 92054C
- Authority
- FI
- Finland
- Prior art keywords
- methoxyphenoxy
- methyl
- oxo
- ether
- propanediol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- GNXFOGHNGIVQEH-UHFFFAOYSA-N 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate Chemical compound COC1=CC=CC=C1OCC(O)COC(N)=O GNXFOGHNGIVQEH-UHFFFAOYSA-N 0.000 title description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- -1 o-methoxyphenoxy Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- FPANKWJAKOGTMU-UHFFFAOYSA-N 1-methoxy-2-propoxybenzene Chemical group CCCOC1=CC=CC=C1OC FPANKWJAKOGTMU-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- YUEATNYGWBDCEL-UHFFFAOYSA-N 1-hydroxypropyl carbamate Chemical compound CCC(O)OC(N)=O YUEATNYGWBDCEL-UHFFFAOYSA-N 0.000 claims 1
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 claims 1
- 241000269821 Scombridae Species 0.000 claims 1
- 235000013351 cheese Nutrition 0.000 claims 1
- BXNKCKFDLBMOTA-UHFFFAOYSA-N dioxol-3-one Chemical compound O=C1C=COO1 BXNKCKFDLBMOTA-UHFFFAOYSA-N 0.000 claims 1
- 238000011010 flushing procedure Methods 0.000 claims 1
- 235000020640 mackerel Nutrition 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960001867 guaiacol Drugs 0.000 description 3
- 229960002330 methocarbamol Drugs 0.000 description 3
- SYZWCZWQBAZDEA-UHFFFAOYSA-N 6-methoxy-5-[(1-methoxy-5-propyl-7-oxabicyclo[4.1.0]hepta-3,5-dien-2-yl)oxy]-2-propyl-7-oxabicyclo[4.1.0]hepta-1,3-diene Chemical compound C(CC)C1=C2C(C(C=C1)OC1C3(C(=C(C=C1)CCC)O3)OC)(O2)OC SYZWCZWQBAZDEA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- LMQRNRKIACTFHG-UHFFFAOYSA-N chloromethylbenzene;n,n-diethylethanamine Chemical compound CCN(CC)CC.ClCC1=CC=CC=C1 LMQRNRKIACTFHG-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3807522A DE3807522C1 (enrdf_load_stackoverflow) | 1988-03-08 | 1988-03-08 | |
| DE3807522 | 1988-03-08 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI891068A0 FI891068A0 (fi) | 1989-03-07 |
| FI891068L FI891068L (fi) | 1989-09-09 |
| FI92054B FI92054B (fi) | 1994-06-15 |
| FI92054C true FI92054C (fi) | 1994-09-26 |
Family
ID=6349127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI891068A FI92054C (fi) | 1988-03-08 | 1989-03-07 | Menetelmä 3-(o-metoksifenoksi)-1,2-propaanidioli-1-karbamaatin valmistamiseksi |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE3807522C1 (enrdf_load_stackoverflow) |
| FI (1) | FI92054C (enrdf_load_stackoverflow) |
| FR (1) | FR2628420B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2216520B (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093456A (en) * | 1989-06-14 | 1992-03-03 | Minnesota Mining And Manufacturing Company | Monocarbamate diols, polymers derived from them and nlo-active materials therefrom |
| WO1998051680A1 (en) * | 1997-05-12 | 1998-11-19 | Daiso Co., Ltd. | Process for producing 1,4-benzodioxane derivatives |
| CN101838249B (zh) * | 2010-03-19 | 2015-08-19 | 浙江华海药业股份有限公司 | 一种制备高纯度愈创木酚缩水甘油醚的方法 |
| CN106349112A (zh) * | 2016-08-24 | 2017-01-25 | 浙江海洲制药有限公司 | 美索巴莫β异构体的制备方法 |
| CN115043811A (zh) * | 2022-06-10 | 2022-09-13 | 苏州敬业医药化工有限公司 | 一种4-[(2-甲氧苯氧基)甲基]-1,3-二氧戊环-2-酮的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB861960A (en) * | 1957-01-22 | 1961-03-01 | A H Robins Company Ltd | Preparation of monocarbamates |
| DE1249852B (de) * | 1964-10-07 | 1967-09-14 | Dr Christian Brunnengraber Che mische Fabrik &. Co mbH Lübeck | Verfahren zur Herstellung von Carbamm saureestern von a Glycermathern |
-
1988
- 1988-03-08 DE DE3807522A patent/DE3807522C1/de not_active Expired
-
1989
- 1989-03-07 GB GB8905218A patent/GB2216520B/en not_active Expired - Fee Related
- 1989-03-07 FR FR8902977A patent/FR2628420B1/fr not_active Expired - Lifetime
- 1989-03-07 FI FI891068A patent/FI92054C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2628420A1 (fr) | 1989-09-15 |
| DE3807522C1 (enrdf_load_stackoverflow) | 1989-03-30 |
| FR2628420B1 (fr) | 1993-08-20 |
| FI891068A0 (fi) | 1989-03-07 |
| FI891068L (fi) | 1989-09-09 |
| GB8905218D0 (en) | 1989-04-19 |
| FI92054B (fi) | 1994-06-15 |
| GB2216520B (en) | 1991-06-26 |
| GB2216520A (en) | 1989-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BOEHRINGER INGELHEIM KG |