GB1201209A - PREPARATION OF SUBSTITUTED OF UNSUBSTITUTED 2-(o- OR p-NITROPHENYL) ALKANOL - Google Patents
PREPARATION OF SUBSTITUTED OF UNSUBSTITUTED 2-(o- OR p-NITROPHENYL) ALKANOLInfo
- Publication number
- GB1201209A GB1201209A GB2852468A GB2852468A GB1201209A GB 1201209 A GB1201209 A GB 1201209A GB 2852468 A GB2852468 A GB 2852468A GB 2852468 A GB2852468 A GB 2852468A GB 1201209 A GB1201209 A GB 1201209A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrophenyl
- substituted
- nitrotoluene
- ethanol
- sulphoxide
- 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
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 3
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- -1 N-substituted amide Chemical class 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 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 abstract 1
- SLRIOXRBAPBGEI-UHFFFAOYSA-N 2-(2-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC=C1[N+]([O-])=O SLRIOXRBAPBGEI-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- VECXEBRNGRTEDI-UHFFFAOYSA-N 2-[2-(2-nitrophenyl)ethenyl]furan Chemical group O1C(=CC=C1)C=CC1=C(C=CC=C1)[N+](=O)[O-] VECXEBRNGRTEDI-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- KBYQXXYMPYFXGR-UHFFFAOYSA-N 4-chloro-1-methyl-2-nitrobenzene 2-nitroethylbenzene Chemical compound ClC1=CC(=C(C=C1)C)[N+](=O)[O-].[N+](=O)([O-])CCC1=CC=CC=C1 KBYQXXYMPYFXGR-UHFFFAOYSA-N 0.000 abstract 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
Abstract
1,201,209. 2-(Nitrophenyl) alkanols. BOFORS A.B. 14 June, 1968 [14 June, 1967], No. 28524/68. Heading C2C. The invention relates to a method of preparing a substituted or unsubstituted 2-(o- or pnitrophenyl) alkanol by reacting a substituted or unsubstituted o- or p-mononitro-alkyl benzene preferably having the general formula in which one of the groups R 2 , R 4 and R 6 is a nitro group, and the remaining groups R 2 -R 8 are the same or different and are each hydrogen or a substituent such as a halogen atom or an alkyl or aryl group with an aldehyde having no α-hydrogen atom in a dialkyl-sulphoxide or N-substituted amide, e.g. dimethyl sulphoxide or formamide as solvent and in the presence of a strong base, e.g. an alkali metal hydroxide in solid aqueous or alcoholic solutions or an alkali metal methylate or an alkali metal ethylate, specified nitro alkyl benzenes are o- or p-nitrotoluene, o-nitroethyl benzene 4-chloro-2-nitrotoluene or 2-(o-nitrophenyl) ethanol. Specified aldehydes are formaldehyde, furfural, benzaldehyde, or a substituted benzaldehyde, wherein the substituent is non-reactive with the base employed. In an example, 4-chloro-2- nitrotoluene and para-formaldehyde are dissolved in dimethyl-sulphoxide and potassium hydroxide added in methanol and subjected to distillation in 2-(4-chloro-2-nitrophenyl) ethanol subsequently obtained. In another example, o-nitrotoluene and furfural are dissolved in dimethyl sulphoxide to which sodium dissolved in ethanol is added and CO 2 passed through. Subsequent distillation yielded 1-(2-furyl)-2- (2-nitrophenyl) ethylene and 1-(2-furyl)-2- (2-nitrophenyl) ethanol. Many other examples are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE839967A SE375759B (en) | 1967-06-14 | 1967-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1201209A true GB1201209A (en) | 1970-08-05 |
Family
ID=20273965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2852468A Expired GB1201209A (en) | 1967-06-14 | 1968-06-14 | PREPARATION OF SUBSTITUTED OF UNSUBSTITUTED 2-(o- OR p-NITROPHENYL) ALKANOL |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH500938A (en) |
| DE (1) | DE1768627B1 (en) |
| FR (1) | FR1568656A (en) |
| GB (1) | GB1201209A (en) |
| SE (1) | SE375759B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4497966A (en) * | 1982-09-14 | 1985-02-05 | Shell Oil Company | Process for the preparation of nitrophenylalkanols |
| US4933505A (en) * | 1988-08-05 | 1990-06-12 | Northwestern University | Method of preparing stereospecific nitroaldols |
| CN114409545A (en) * | 2022-01-26 | 2022-04-29 | 江苏飞宇医药科技股份有限公司 | Method for continuously preparing 2- (2-nitrophenyl) ethanol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3064382D1 (en) * | 1979-05-16 | 1983-09-01 | Siegfried Ag | Use of chloronitrophenyl derivatives as selective herbicides and new chloronitrophenyl derivatives |
| GB8607557D0 (en) * | 1986-03-26 | 1986-04-30 | Wendstone Chemicals | Chemical compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046600B (en) * | 1956-02-24 | 1958-12-18 | Degussa | Process for the production of ª ‰ -nitroaethanol |
-
1967
- 1967-06-14 SE SE839967A patent/SE375759B/xx unknown
-
1968
- 1968-06-07 CH CH844168A patent/CH500938A/en not_active IP Right Cessation
- 1968-06-08 DE DE19681768627 patent/DE1768627B1/en 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4497966A (en) * | 1982-09-14 | 1985-02-05 | Shell Oil Company | Process for the preparation of nitrophenylalkanols |
| US4933505A (en) * | 1988-08-05 | 1990-06-12 | Northwestern University | Method of preparing stereospecific nitroaldols |
| CN114409545A (en) * | 2022-01-26 | 2022-04-29 | 江苏飞宇医药科技股份有限公司 | Method for continuously preparing 2- (2-nitrophenyl) ethanol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768627B1 (en) | 1972-05-25 |
| SE375759B (en) | 1975-04-28 |
| FR1568656A (en) | 1969-05-23 |
| CH500938A (en) | 1970-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ji et al. | Copper-catalyzed aerobic oxygenative cross dehydrogenative coupling of methyl ketones with para-C–H of primary anilines | |
| GB1201209A (en) | PREPARATION OF SUBSTITUTED OF UNSUBSTITUTED 2-(o- OR p-NITROPHENYL) ALKANOL | |
| SU482943A3 (en) | Method for producing alkanolamine derivatives | |
| GB1332477A (en) | Basic azo dyes free from sulphonic acid groups their production and use | |
| DE1809386A1 (en) | Process for the preparation of 1,5-disubstituted 4-cyanopyrazoles | |
| GB1001821A (en) | Light-sensitive elements for photomechanical reproduction | |
| US2563325A (en) | Acetalsof propargyt abc | |
| GB459878A (en) | Polyvinyl acetal resins | |
| GB1445707A (en) | Imidazolyl-indane and imidazolyl-tetralin derivatives | |
| US3798234A (en) | Process for the preparation of 3-anilino-pyrazolones-(5) | |
| Scott et al. | New Compounds. Some Aldehydic Hydrazones of Triaiminoguanidine | |
| Levy et al. | The aliphatic nitro-compounds | |
| US2543267A (en) | Hydroxyethyl-acylamidobiphenylyl ketones | |
| CH445492A (en) | Process for the preparation of a- (3-indolyl) -lower aliphatic acids acylated in the 1-position | |
| US2862034A (en) | X-dibenzyloxy-x-nitrostyrenes | |
| GB1134701A (en) | Imidazolidine derivatives | |
| US2545092A (en) | Acylamido-hydroxy-propionaphthones | |
| US2460265A (en) | Arylalkylnitroalcohols | |
| Dains et al. | THE REDUCTION OF AROMATIC NITRO AND NITROSO COMPOUNDS WITH SODIUM ALCOHOLATES. II. | |
| US2990411A (en) | Polynitro compounds | |
| US3846493A (en) | Nitro substituted acrylic acid amides | |
| US3185711A (en) | Oxobutyrolactones | |
| SU122145A1 (en) | The method of obtaining nitrospirt | |
| SU122817A1 (en) | Method of anaphoretic coating of cathode heaters of radio tubes | |
| ES424429A1 (en) | 3-n-butyl-amino-4-phenoxy-5-sulphamoyl-benzoic acids and process for their manufacture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |