2-Butene, 1-bromo- → Methyl 3-(2-buten-1-yloxy)-5-methoxybenzoate

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Reaction Steps

3,5-Dimethoxy-4-(1-methyl) propyl-benzoyl chloride. Starting from 3-hydroxy-5-methoxy-benzoic acid methyl ester by reaction with 2-butenylbromide, 3-(2-butenyloxy)-5-methoxy-benzoic acid methyl ester is obtained. B.p. 156°-58°C/0.4 mmHg. By operating as described under C) the 3,5-dimethoxy-4-(3-methylpropen-3-yl)-benzoic acid is obtained. M.p. 140°-41°C (from diethyl ether/light petroleum). This compound is hydrogenated as under D) to give 3,5-dimethoxy-4-(1-methyl)propyl-benzoic acid, m.p. 125°-26°C (from diethyl ether/light petroleum). This compound is allowed to react with thionyl chloride, thus obtaining the title compound. M.p. 47°-48°C (from diethyl ether upon cooling).

Provenance & Evidence