GB901205A - Improvements in or relating to the production of aromatic mixed aliphatic-aromatic or aromatic thienyl ketones - Google Patents
Improvements in or relating to the production of aromatic mixed aliphatic-aromatic or aromatic thienyl ketonesInfo
- Publication number
- GB901205A GB901205A GB2504258A GB2504258A GB901205A GB 901205 A GB901205 A GB 901205A GB 2504258 A GB2504258 A GB 2504258A GB 2504258 A GB2504258 A GB 2504258A GB 901205 A GB901205 A GB 901205A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aromatic
- salt
- compound
- reacting
- aliphatic
- 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
- -1 aromatic thienyl ketones Chemical class 0.000 title abstract 3
- 125000003118 aryl group Chemical group 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000008064 anhydrides Chemical class 0.000 abstract 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 2
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 abstract 1
- MKTIYCMWJSUVOT-UHFFFAOYSA-N 4-methoxy-1-phenyloctadecan-1-one Chemical compound COC(CCC(=O)C1=CC=CC=C1)CCCCCCCCCCCCCC MKTIYCMWJSUVOT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 abstract 1
- 102100024864 REST corepressor 1 Human genes 0.000 abstract 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- PEVZEFCZINKUCG-UHFFFAOYSA-L copper;octadecanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O PEVZEFCZINKUCG-UHFFFAOYSA-L 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 235000011180 diphosphates Nutrition 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229940048084 pyrophosphate Drugs 0.000 abstract 1
- 229940005657 pyrophosphoric acid Drugs 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Aromatic, mixed aliphatic-aromatic or aromatic-thienyl ketones are prepared by reacting together a halide or salt of a monocarboxylic acid of the general formula R1.COOH with respectively a salt or a halide of ortho, meta or pyro-phosphoric acid or a mixture thereof to form a mixed anhydride, R1 in the formula representing an aliphatic, aliphatic-aromatic or aromatic hydrocarbon radical from which free hydroxy, sulphydryl and amino groups are absent, and said salt of the carboxylic or phosphoric acid being a salt of a metal other than an alkali or alkaline earth metal, and reacting the resulting mixed anhydride with an aromatic compound RH where R represents a phenyl or naphthyl residue substituted by at least two hydrocarbon radicals or by at least one ether group or by at least one mono- or di-acylamino group, or where R represents an unsubstituted thienyl residue, so as to produce a ketone of the formula RCOR1. The mixed anhydride may be prepared and isolated and then reacted with the compound RH or alternatively the salt and halide may be reacted in the presence of the compound RH e.g. at 100-150 DEG C. in the presence of a diluent such as a nitroparaffin or excess RH. A trace of water may be added to the reactants to facilitate reaction. In examples silver ortho, meta or pyrophosphate is reacted with an aromatic carboxylic acid chloride and the resulting anhydride with the compound RH to give phenyl thienyl ketone and 4 - acetylamino-, 21 - chloro-4-methoxy-, 2,4,6-trimethyl and 4-methoxy-benzophenone; the last mentioned compound is also prepared by reacting silver benzoate, phosphorus oxychloride and anisole and 4-methoxy-stearophenone by reacting cupric stearate, phosphorous oxychloride and anisole.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL219745 | 1957-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB901205A true GB901205A (en) | 1962-07-18 |
Family
ID=19750947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2504258A Expired GB901205A (en) | 1957-08-08 | 1958-08-05 | Improvements in or relating to the production of aromatic mixed aliphatic-aromatic or aromatic thienyl ketones |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE570178A (en) |
| FR (1) | FR1214887A (en) |
| GB (1) | GB901205A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046337A2 (en) * | 1980-08-20 | 1982-02-24 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
-
0
- BE BE570178D patent/BE570178A/xx unknown
-
1958
- 1958-08-05 GB GB2504258A patent/GB901205A/en not_active Expired
- 1958-08-07 FR FR772109A patent/FR1214887A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046337A2 (en) * | 1980-08-20 | 1982-02-24 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
| EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| BE570178A (en) | |
| FR1214887A (en) | 1960-04-12 |
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