SYNTHETIC APPLICATION 19closure of 2-(Y,Y-dimethylallyl)-phenol gives only the chroman LXVIII,irrespective of the presence or absence of peroxides.29Treatment of 2-allylphenols with mercuric salts gives mercurimethyl--CHCH2HgXLXIX LXXdihydrobenzofurans such as LXIX.79-80'81The halomercuri group canbe replaced by iodine by treatment with potassium iodide, and this is amethod of preparing iodo compounds like LXX.Another occasionally useful transformation of allylphenols is theisomerization to propenylphenols by strong alkali, as in the well-knownisomerization of eugenol to isoeugenol. For example, 2-methoxy-6-allylphenol (LXXI) is changed to the propenyl compound LXXII byOHLXXI LXXIIheating 1 part of the phenol with 2 parts of powdered potassium hydrox-ide and 1 of water for one hour at 170°.* This isomerization also can bebrought about by heating with soda lime without solvent/ but thephenolic hydroxyl must be etherified.
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