Hydrogen Bromide → Benzenenonanoic acid, 4-hydroxy-

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Reaction Steps

In step 1 of this synthetic sequence, the ether group of 9(4-methoxyphenyl)nonanoic acid is cleaved with hydrogen bromide to give the alcohol, 9(4-hydroxyphenyl)nonanoic acid. In step 2, this acid is converted to its methyl ester. In step 3, the 9(4-hydroxyphenyl)nonanoic acid, methyl ester is alkylated (with n-butyl or n-hexyl bromide) and then hydrolyzed to give 9(4-alkoxyphenyl)nonanoic acids. In step 4, the acid is converted to the acid chloride, using thionyl chloride. In step 5, the acid chloride is condensed with a substituted or unsubstituted hydroxylamine to give the final product.

Provenance & Evidence