GB748304A - Diaryl hexanoic acid derivatives - Google Patents

Diaryl hexanoic acid derivatives

Info

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
Application number
GB2407153A
Inventor
Everett Maynard Schultz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Priority to GB2407153A priority Critical patent/GB748304A/en
Publication of GB748304A publication Critical patent/GB748304A/en
Expired legal-status Critical Current

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.
GB2407153A 1953-08-31 1953-08-31 Diaryl hexanoic acid derivatives Expired GB748304A (en)

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)

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