5,6-Dimethyl-2,3-dihydro-1H-indene-1-one

5,6-Dimethyl-2,3-dihydro-1H-indene-1-one Property

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light yellow to yellow Solid

Safety

HS Code 

2914390090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5,6-Dimethyl-2,3-dihydro-1H-indene-1-one Chemical Properties,Usage,Production

Synthesis

A mixture of 48 mL (0.4 mol) of o-xylene with 50 g of 3-chloropropionyl chloride was slowly added dropwise to a suspension containing 116 g (0.87 mol) of aluminum chloride and 200 mL of nitromethane under ice bath conditions. After the dropwise addition, the reaction system was slowly warmed to room temperature and stirring was continued for 5 hours. Subsequently, the reaction mixture was poured into a pre-cooled mixture of 1 N hydrochloric acid and ice water and stirred thoroughly. The organic phase was separated and washed sequentially with 1N hydrochloric acid, water and saturated brine and finally dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the intermediate solid. The solid was added to 300 mL of concentrated sulfuric acid in batches and heated and stirred in an oil bath at 100 °C for 4 h. About 40% of the cyclic isomer by-product was generated in this process. Upon completion of the reaction, the reaction solution was quenched by pouring it into ice water and extracted with diethyl ether. The organic phase was washed sequentially with water and saturated saline, and then dried with anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was purified by recrystallization from hot hexane to remove the cyclic isomer. Finally 25.5 g of 5,6-dimethyl-2,3-dihydro-1H-inden-1-one was obtained in 40% yield.

References

[1] Patent: JP2015/193605, 2015, A. Location in patent: Paragraph 0130