公开(公告)号：FR1206978A

公开(公告)日：1960-02-12

申请号：FR1206978D

申请日：1958-05-27

Applicant: BASF AG

Inventor： BECKE FRIEDRICH ,  BITTERMANN HERBERT

IPC: C07C45/46 ,  C07C49/782 ,  C07C49/813 ,  C07C49/84

公开(公告)号：GB825473A

公开(公告)日：1959-12-16

申请号：GB1612158

申请日：1958-05-20

Applicant: BASF AG

Inventor： BECKE FRIEDRICH ,  BITTERMANN HERBERT

IPC: C07C45/46 ,  C07C49/782 ,  C07C49/813 ,  C07C49/84

Abstract: Benzylacetophenones of the general formula 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 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.