DE1768627B1 - Verfahren zur Herstellung von 2-(o- oder p-Nitrophenyl)-alkanolen - Google Patents
Verfahren zur Herstellung von 2-(o- oder p-Nitrophenyl)-alkanolenInfo
- Publication number
- DE1768627B1 DE1768627B1 DE19681768627 DE1768627A DE1768627B1 DE 1768627 B1 DE1768627 B1 DE 1768627B1 DE 19681768627 DE19681768627 DE 19681768627 DE 1768627 A DE1768627 A DE 1768627A DE 1768627 B1 DE1768627 B1 DE 1768627B1
- Authority
- DE
- Germany
- Prior art keywords
- nitrotoluene
- ethanol
- added
- nitrophenyl
- mol
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 10
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 title claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 52
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical group CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 27
- 235000019441 ethanol Nutrition 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 15
- 229930040373 Paraformaldehyde Natural products 0.000 description 14
- 229920002866 paraformaldehyde Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- SLRIOXRBAPBGEI-UHFFFAOYSA-N 2-(2-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC=C1[N+]([O-])=O SLRIOXRBAPBGEI-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- -1 methoxyphenyl Chemical group 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 5
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical class COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- SQFLFRQWPBEDHM-UHFFFAOYSA-N 4-chloro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C=C1[N+]([O-])=O SQFLFRQWPBEDHM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- CIVPZPJJPWVVIP-UHFFFAOYSA-N 2-(2-nitrophenyl)propan-1-ol Chemical compound OCC(C)C1=CC=CC=C1[N+]([O-])=O CIVPZPJJPWVVIP-UHFFFAOYSA-N 0.000 description 2
- IKMXRUOZUUKSON-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanol Chemical compound OCCC1=CC=C([N+]([O-])=O)C=C1 IKMXRUOZUUKSON-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 description 1
- ITWGFVBULTWHHD-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-methyl-6-nitrobenzene Chemical compound CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1[N+]([O-])=O ITWGFVBULTWHHD-UHFFFAOYSA-N 0.000 description 1
- LMBVRMXWPHODOO-UHFFFAOYSA-N 1,2-bis(2-nitrophenyl)ethanol Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C(CC1=C(C=CC=C1)[N+](=O)[O-])O LMBVRMXWPHODOO-UHFFFAOYSA-N 0.000 description 1
- DSDBYQDNNWCLHL-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1[N+]([O-])=O DSDBYQDNNWCLHL-UHFFFAOYSA-N 0.000 description 1
- UOIYIXIGEVVHLE-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-(2-nitrophenyl)ethanol Chemical compound C1=CC(OC)=CC=C1C(O)CC1=CC=CC=C1[N+]([O-])=O UOIYIXIGEVVHLE-UHFFFAOYSA-N 0.000 description 1
- FYGDBRVOWVZMTA-UHFFFAOYSA-N 1-(furan-2-yl)-2-(2-nitrophenyl)ethanol Chemical compound C=1C=COC=1C(O)CC1=CC=CC=C1[N+]([O-])=O FYGDBRVOWVZMTA-UHFFFAOYSA-N 0.000 description 1
- FLKQZNFLWOPRFX-UHFFFAOYSA-N 2-(2-chloro-6-nitrophenyl)ethanol Chemical compound OCCC1=C(Cl)C=CC=C1[N+]([O-])=O FLKQZNFLWOPRFX-UHFFFAOYSA-N 0.000 description 1
- KZJIJJUXIGOECZ-UHFFFAOYSA-N 2-(2-nitrophenyl)propane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1[N+]([O-])=O KZJIJJUXIGOECZ-UHFFFAOYSA-N 0.000 description 1
- BCYIUCVPTJDUPV-UHFFFAOYSA-N 2-(2-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1[N+]([O-])=O BCYIUCVPTJDUPV-UHFFFAOYSA-N 0.000 description 1
- ZLIUZAQTMIMCIN-UHFFFAOYSA-N 2-(4-chloro-2-nitrophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1[N+]([O-])=O ZLIUZAQTMIMCIN-UHFFFAOYSA-N 0.000 description 1
- XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 description 1
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
- PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical compound [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE839967A SE375759B (OSRAM) | 1967-06-14 | 1967-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768627B1 true DE1768627B1 (de) | 1972-05-25 |
Family
ID=20273965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768627 Withdrawn DE1768627B1 (de) | 1967-06-14 | 1968-06-08 | Verfahren zur Herstellung von 2-(o- oder p-Nitrophenyl)-alkanolen |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH500938A (OSRAM) |
| DE (1) | DE1768627B1 (OSRAM) |
| FR (1) | FR1568656A (OSRAM) |
| GB (1) | GB1201209A (OSRAM) |
| SE (1) | SE375759B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0239354A3 (en) * | 1986-03-26 | 1989-08-09 | Wendstone Chemicals P.L.C. | 2,2-dinitrophenylethane derivatives and their application as protecting compounds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56500535A (OSRAM) * | 1979-05-16 | 1981-04-23 | ||
| HU177886B (en) | 1979-05-29 | 1982-01-28 | Reanal Finomvegyszergyar | Process for the selective hydroxymethylation of nitro-toluenes |
| DE3369123D1 (en) * | 1982-09-14 | 1987-02-19 | Shell Int Research | Process for the preparation of nitrophenylalkanols |
| US4933505A (en) * | 1988-08-05 | 1990-06-12 | Northwestern University | Method of preparing stereospecific nitroaldols |
| CN114409545A (zh) * | 2022-01-26 | 2022-04-29 | 江苏飞宇医药科技股份有限公司 | 一种连续制备2-(2-硝基苯基)乙醇的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046600B (de) * | 1956-02-24 | 1958-12-18 | Degussa | Verfahren zur Herstellung von ª‰-Nitroaethanol |
-
1967
- 1967-06-14 SE SE839967A patent/SE375759B/xx unknown
-
1968
- 1968-06-07 CH CH844168A patent/CH500938A/de not_active IP Right Cessation
- 1968-06-08 DE DE19681768627 patent/DE1768627B1/de not_active Withdrawn
- 1968-06-13 FR FR1568656D patent/FR1568656A/fr not_active Expired
- 1968-06-14 GB GB2852468A patent/GB1201209A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046600B (de) * | 1956-02-24 | 1958-12-18 | Degussa | Verfahren zur Herstellung von ª‰-Nitroaethanol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0239354A3 (en) * | 1986-03-26 | 1989-08-09 | Wendstone Chemicals P.L.C. | 2,2-dinitrophenylethane derivatives and their application as protecting compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CH500938A (de) | 1970-12-31 |
| SE375759B (OSRAM) | 1975-04-28 |
| FR1568656A (OSRAM) | 1969-05-23 |
| GB1201209A (en) | 1970-08-05 |
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