Indane → 3,5,6,7-Tetrahydro-2-methyl-s-indacen-1(2H)-one

Participants

Reaction Steps

50.71 g (377 mmol) of anhydrous aluminum trichloride were slowly added at 0° C. to a mixture of 19.3 g (163 mmol) of indane and 38.3 g of 2-bromoisobutyryl bromide in 500 ml of methylene chloride over a period of 30 minutes. The reaction mixture became dark red. The suspension was stirred at room temperature for 17 hours and subsequently poured onto 200 g of ice. The phases were separated. The organic phase was washed once with 200 ml of 1 normal hydrochloric acid, twice with 200 ml each time of saturated sodium hydrogencarbonate solution and twice with 200 ml each time of water. The organic phase was dried over anhydrous sodium sulfate and filtered. Removal of the solvent under reduced pressure gave 30 g (99% yield) of the compound (1a) as reddish brown oil. According to GC-MS, the content of (1a) in the oil was 99%.

Provenance & Evidence