GB748304A - Diaryl hexanoic acid derivatives - Google Patents
Diaryl hexanoic acid derivativesInfo
- Publication number
- GB748304A GB748304A GB2407153A GB2407153A GB748304A GB 748304 A GB748304 A GB 748304A GB 2407153 A GB2407153 A GB 2407153A GB 2407153 A GB2407153 A GB 2407153A GB 748304 A GB748304 A GB 748304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- acid
- tolyl
- chlorophenyl
- acrylonitrile
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises hexanoic acid derivatives of the formula <FORM:0748304/IV(a)/1> where X is nitrile, carboxylic acid, or salt or ester thereof, and Y is hydrogen, halogen, alkyl or alkoxy (1-5 carbon atoms), excluding those in which the Y substituents are both meta. The compounds are made by reacting 1 : 1-diarylpropanones with acrylonitrile and, if desired, hydrolysing the product to the acid and esterifying or forming a salt thereof. The 1 : 1 diaryl-propanones are made from 1-arylpropanones by halogenation and Friedel-Crafts condensation with benzene or a Y-substituted benzene. In the examples: (1) diphenylacetone is reacted with acrylonitrile in t.-butyl alcohol in the presence of benzyltrimethylammonium hydroxide to give 4 : 4-diphenyl-5-oxocapronitrile; (2) the nitrile of (1) is hydrolysed to 4 : 4-diphenyl-5-oxocaproic acid; (3) p-chlorophenylacetone is brominated and condensed with benzene to give 1-phenyl-1-(p-chlorophenyl)-acetone, which is reacted with acrylonitrile as in (1) to yield 4-phenyl-4-(p-chlorophenyl) - 5 - oxocapronitrile; (4) the preceding nitrile is hydrolysed to the free acid; (5) as in (3) the starting material being obtained by brominating phenylacetone and condensing the product with chlorobenzene; the 2 : 4-dinitrophenylhydrazone is described; (6) phenylacetone is brominated and condensed with toluene to give 1-phenyl-1-(p-tolyl)-propanone, which is reacted with acrylonitrile to form 4-phenyl - 4 - (p - tolyl) - 5 - oxo - capronitrile, hydrolysed to the free acid; (7) m-methoxyphenylacetone is brominated and condensed with benzene to yield 1-phenyl-1-(m-methoxyphenyl)-propanone, from which are obtained 4 - phenyl - 4 - (m - methoxyphenyl) - 5 - oxocapronitrile and 4 - phenyl - 4 - (m - methoxyphenyl) - 5 - oxocaproic acid; (8) 4 : 4-diphenyl-5-oxocaproic is esterified with methanol and ethanol in the presence of sulphuric acid. Other specified products are those in which one aryl group is phenyl and the other is m- or p-bromophenyl, m-chlorophenyl, p-ethylphenyl, p-butylphenyl and m- and p-ethoxyphenyl, also the di-(p-chlorophenyl), di-(p-tolyl) and p-tolyl-p-propylphenyl compounds.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2407153A GB748304A (en) | 1953-08-31 | 1953-08-31 | Diaryl hexanoic acid derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2407153A GB748304A (en) | 1953-08-31 | 1953-08-31 | Diaryl hexanoic acid derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB748304A true GB748304A (en) | 1956-04-25 |
Family
ID=10205909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2407153A Expired GB748304A (en) | 1953-08-31 | 1953-08-31 | Diaryl hexanoic acid derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB748304A (en) |
-
1953
- 1953-08-31 GB GB2407153A patent/GB748304A/en not_active Expired
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