Hydrochloric Acid → 2-(5-Chloro-1H-inden-3-yl)phenyl methyl ether

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Reaction Steps

Under an argon atmosphere, a solution of 12.80 g of 6-chloroindan-1-one (73.45 mol) from Example 16A in 60 ml of THF is added drop wise to 88 ml of a 1 M solution of 2-methoxyphenylmagnesium bromide in THF (88.0 mol) at 0° C. The reaction mixture is stirred at room temperature for 1.5 h and 200 ml of 1 N hydrochloric acid are added for working up. The mixture is extracted three times with ethyl acetate, the combined organic phases are dried over sodium sulphate, and the solvent is removed in a rotary evaporator. The residue is dissolved in 400 ml of dichloromethane, mixed with 0.10 g of 4-toluenesulphonic acid monohydrate (0.53 mol) and stirred at room temperature for 16 h. The reaction mixture is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution and dried over sodium sulphate. The solvent is removed in a rotary evaporator, and the residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 150:1). 12.02 g (61% of theory) of the title compound are obtained.

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