Abstract
The treatment of l, 2, 3, 4, 4a, 9b-hexahydro-3, 8-dihydroxy-7-methoxy-9b-(2'-methoxyethyl)dibenzofuran with chloroform and aqueous potassium hydroxide under conventional Reimer-Tiemann reaction conditions resulted in the replacement of the 7-methoxyl group by a carbaldehyde one. A choice between alternative pathways for this novel displacement has been facilitated by examination of the behaviour of the corresponding 7-trideuteromethoxy compound. Dichlorocarbene attack at position 7 rather than at the unsubstituted position 9 is shown to be due to steric encumbrance at the latter site.
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