2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE

Originator

Uvistat-L,Ward Blenkinsop,UK,1960

The Uses of 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE

sunscreen

The Uses of 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE

2-Hydroxy-4-methoxy-4'-methyl-benzophenone is an UV absorbing agent in sunscreen cosmetic creams, lotions, lipstieks, sun oils, etc.

Preparation

Preparation by Friedel–Crafts acylation of m-methoxy-phenol with p-toluoyl chloride,
in the presence of boron trichloride in benzene first at ?10°, then at reflux for 10 h under nitrogen (80%)
in the presence of titanium tetrachloride in benzene first at ?10°, then at reflux for 14 h under nitrogen (73%) or in chlorobenzene for 1 h at 120° (79%).

Definition

ChEBI: Mexenone is a member of benzophenones.

Manufacturing Process

p-Toluoyl chloride is the starting material. To this is added chlorobenzene and 1,3-dimethoxybenzene. The reaction mixture is cooled to 12°C in an ice bath and aluminum chloride is added gradually, keeping the reaction below 30°C. The reaction is then gradually heated to 115°C with the evolution of hydrogen chloride gas. As the temperature increases, the reaction mixture becomes thicker. At 105°C, dimethyl formamide is added slowly. The reaction is heated at 115°C for a short time and is then poured into concentrated hydrochloric acid. The reaction mixture pours very easily and very cleanly. The acid mixture is heated with steam to dissolve all the material which had not hydrolyzed and the mixture is filtered. The red chlorobenzene layer is separated and washed twice with hot water.
To the chlorobenzene solution is then added sodium hydroxide dissolved in water and the chlorobenzene is removed by a steam distillation. After all of the chlorobenzene is removed, the precipitate which forms during the distillation is removed by filtration and discarded. The solution is cooled and acidified with hydrochloric acid, precipitating a tan solid. This is removed by filtration and washed acid-free. It is then treated with sodium bicarbonate solution to remove any acid present and is then washed with water to remove all traces of bicarbonate. After drying approximately a 75% yield of mexenone is obtained.

Therapeutic Function

Sunscreen agent

Contact allergens

BZP-10 is exceptionally positive in ketoprofen-photosensitive patients.