Iodine → (2-Chloro-4,5-dihydroxyphenyl)phenylmethanone

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Reaction Steps

The afore-mentioned dihydroxyketone can also be obtained in two stages analogously to Example 9(a) and (b). The (2-chloro-4,5-dimethoxyphenyl)-phenylmethanone required for this purpose can be obtained by acylating 4-chloro-1,2-dimethoxybenzene with benzoyl chloride in the presence of iodine. It is easier to obtain, however, if one equivalent of 4-chloro-1,2-dimethoxybenzene is heated in a bomb tube at 150° for 2 hours with 1.1 equivalents of (2-pyridinyl)-benzoate in trifluoroacetic acid. After working up and demethylation in a manner analogous to Example 9(b), the desired (4,5-dihydroxy-2-chlorophenyl)phenylmethanone is obtained.

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