GB825473A - Improvements in the production of benzylacetophenones - Google Patents

Improvements in the production of benzylacetophenones

Info

Publication number
GB825473A
GB825473A GB1612158A GB1612158A GB825473A GB 825473 A GB825473 A GB 825473A GB 1612158 A GB1612158 A GB 1612158A GB 1612158 A GB1612158 A GB 1612158A GB 825473 A GB825473 A GB 825473A
Authority
GB
United Kingdom
Prior art keywords
propanone
bis
benzene
acrylic acid
mixture
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
GB1612158A
Inventor
Friedrich Becke
Herbert Bittermann
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB825473A publication Critical patent/GB825473A/en
Expired legal-status Critical Current

Links

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
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • 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
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Benzylacetophenones of the general formula <FORM:0825473/IV (b)/1> wherein R and R1 represent hydrogen or halogen atoms, or alkyl or alkoxy groups with 1 to 12 carbon atoms, are prepared by reacting an acrylic acid halide with benzene or a benzene derivative of the general formula <FORM:0825473/IV (b)/2> in the presence of a catalyst of the Friedel-Crafts type. For the production of benzyl-acetophenones having different substituents in the two aromatic nuclei, one aromatic component is reacted with a molar amount of the acrylic acid halide, for example at a temperature of 0-20 DEG C., and then the other aromatic component is added in molar excess and the reaction continued at 40-80 DEG C. Examples 1 and 2 describe the preparation of 1,3-bis-anisylpropanone-(1) by the action of acrylic acid chloride on anisole in the presence of aluminium chloride. Example 3 describes the preparation of 1,3-bis-xylyl-propanone-(1). In Example 4, a solution of acrylic acid chloride, obtained by reacting acrylic acid with phosphorus pentachloride in benzene, is added at about 70 DEG C. to a mixture of benzene and aluminium chloride. After stirring for about 3 hours, the reaction mixture is poured on to ice. The organic phase is then washed free from acid, and the unreacted benzene is distilled off. Further distillation yields benzylacetophenone. In Example 5, a mixture of acrylic acid chloride and anisole is slowly added, while stirring and cooling to 0-20 DEG C., to aluminium chloride suspended in carbon disulphide, the reaction-mixture being irradiated with a mercury vapour lamp. After the evolution of hydrogen chloride has subsided, benzene is added, and the reaction-mixture is heated to 60-70 DEG C. for 2-3 hours. The product is poured on to ice, and washed free from acid. After distilling off the carbon disulphide and excess benzene, 1-anisyl-3-phenyl-propanone-(1) is obtained by vacuum distillation. Examples 6 to 10 relate to the preparation of the following compounds: bis-(chlorphenyl)-propanone, bis-(meta-dichlorphenyl)-propanone, bis - (meta - chlortoluyl) - propanone, bis-ethoxyphenyl-propanone, and bis-(isopropylphenyl)-propanone.
GB1612158A 1957-05-28 1958-05-20 Improvements in the production of benzylacetophenones Expired GB825473A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB44779A DE1078560B (en) 1957-05-28 1957-05-28 Process for the preparation of benzylacetophenone or its ring-substituted derivatives

Publications (1)

Publication Number Publication Date
GB825473A true GB825473A (en) 1959-12-16

Family

ID=6967421

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1612158A Expired GB825473A (en) 1957-05-28 1958-05-20 Improvements in the production of benzylacetophenones

Country Status (4)

Country Link
CH (1) CH370398A (en)
DE (1) DE1078560B (en)
FR (1) FR1206978A (en)
GB (1) GB825473A (en)

Also Published As

Publication number Publication date
DE1078560B (en) 1960-03-31
FR1206978A (en) 1960-02-12
CH370398A (en) 1963-07-15

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