Ozone → (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone

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Ozone (3 g ozone/hour) was conducted for 60 minutes while stirring through a solution, cooled to -70°, of 13.6 g of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone in 200 ml of anhydrous dichloromethane and 400 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen and then 6.4 ml of dimethyl sulfide were added to the cold solution. The solution came to room temperature overnight and was evaporated in a vacuum. The residue was dissolved in 1600 ml of dichloromethane. The solution was treated with 600 g of silica gel and 100 ml of 10% oxalic acid solution and stirred overnight. Then, the mixture was filtered and the filtrate was concentrated in a vacuum. 6.5 g (51%) of (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone were obtained as a yellow oil.

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