GB480617A - Process for the introduction of aryl groups into ª -ª -unsaturated carbonyl compounds and their derivatives - Google Patents
Process for the introduction of aryl groups into ª -ª -unsaturated carbonyl compounds and their derivativesInfo
- Publication number
- GB480617A GB480617A GB24321/36A GB2432136A GB480617A GB 480617 A GB480617 A GB 480617A GB 24321/36 A GB24321/36 A GB 24321/36A GB 2432136 A GB2432136 A GB 2432136A GB 480617 A GB480617 A GB 480617A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cumarin
- reacted
- compounds
- copper
- 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
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F04—POSITIVE - DISPLACEMENT MACHINES FOR LIQUIDS; PUMPS FOR LIQUIDS OR ELASTIC FLUIDS
- F04C—ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT MACHINES FOR LIQUIDS; ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT PUMPS
- F04C28/00—Control of, monitoring of, or safety arrangements for, pumps or pumping installations specially adapted for elastic fluids
- F04C28/24—Control of, monitoring of, or safety arrangements for, pumps or pumping installations specially adapted for elastic fluids characterised by using valves controlling pressure or flow rate, e.g. discharge valves or unloading valves
- F04C28/26—Control of, monitoring of, or safety arrangements for, pumps or pumping installations specially adapted for elastic fluids characterised by using valves controlling pressure or flow rate, e.g. discharge valves or unloading valves using bypass channels
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D67/00—Combinations of couplings and brakes; Combinations of clutches and brakes
- F16D67/02—Clutch-brake combinations
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
a - b - Unsaturated non - quinonoid carbonyl compounds such as aldehydes, ketones, or carboxylic acids, and also their derivatives in so far as they contain a hydrogen atom on the a -carbon atom are reacted with aromatic diazonium salts or compounds convertible thereinto such as acylnitrosamines in dilute inorganic acid or in organic acid solution, and at elevated temperature so that nitrogen is split off and the a -hydrogen atom in the carbonyl compound is replaced by an aryl group. Quinonoid compounds are defined as compounds with two carbonyl groups and two double bonds in one cyclohexane ring. There are obtained from benzal acetone or cumarin with diazo compounds a -acetylstilbenes or 3-arylcumarins respectively. In the case of certain a -b -unsaturated carboxylic acids such as cinnamic acid, the carboxyl group is split off as carbon dioxide during the reaction. The arylated a -b -unsaturated carbonyl compounds are sometimes obtained as their hydrogen halide addition products and are treated with agents splitting off hydrogen halide, e.g. by heating with sodium acetate in glacial acetic acid. An addition of copper or copper salts favours the reaction, which can be carried out in strong acetic acid, aqueous-alcoholic or aqueous-acetone solution with the addition of alkali acetates or alkali salts of other weak acids such as the acid to be arylated. Other solvents such as methylene chloride or acetylene tetrachloride may be used. The presence of negative substituents in the diazo compound is favourable. In examples: (1) p-nitrobenzene diazonium chloride is reacted with cumarin in aqueous-acetone solution in presence of sodium acetate and copper sulphate to give 3-p-nitrophenylcumarin; if the diazo compounds from p - chloraniline, b - naphthylamine, p - aminobenzoic acid or sulphanilic acid are used there are obtained 3-p-chlorphenylcumarin, 3-b -naphthylcumarin, 3-phenyl-cumarin-41- carboxylic acid and 3-phenyl-cumarin-41-sulphonic acid; (2) p-chlorbenzene diazonium chloride is reacted with cinnamic acid as in (1) to give small quantities of a -p-chlorphenylcinnamic acid but mainly p-chlorstilbene; if crotonic acid is used, a -p-chlorphenylcrotonic acid is the chief product, but p-chloropropenylbenzene is also obtained; (3) p - chlorbenzene diazonium chloride is reacted with benzal acetone as in (1), but splitting off hydrogen halide from the product to give a -acetyl-p-chlorostilbene; (4) p-chlorbenzene diazonium chloride is reacted with cinnamic aldehyde as in (1) to give a -p-chlorphenyl cinnamic aldehyde; (5) p-chlorbenzene diazonium chloride is reacted with cumarin as in (1) but in absence of copper or a copper salt, to give a small yield of 3-p-chlorphenyl-cumarin; the yield is increased if copper chloride is present.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE480617X | 1915-01-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB480617A true GB480617A (en) | 1938-02-25 |
Family
ID=6542563
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24321/36A Expired GB480617A (en) | 1935-09-17 | 1936-09-05 | Process for the introduction of aryl groups into ª -ª -unsaturated carbonyl compounds and their derivatives |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR480617A (en) |
GB (1) | GB480617A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2977888A (en) * | 1955-02-24 | 1961-04-04 | William T Livermore | Hydraulic pump and control valve assembly |
JPH0794832B2 (en) * | 1988-08-12 | 1995-10-11 | 三菱重工業株式会社 | Rotary compressor |
-
1916
- 1916-01-05 FR FR480617D patent/FR480617A/en not_active Expired
-
1936
- 1936-09-05 GB GB24321/36A patent/GB480617A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR480617A (en) | 1916-08-31 |
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