PURPOSE: 7-Hydroxygeranylamine is isomerized with a mercaptan to an enamine, which is hydrolyzed to produce hydroxycitronellal useful as perfume and its intermediate in high yield.
CONSTITUTION: A compound of formula I, II, III, or IV (R is 1W6C alkyl) is isomerized by using a mercaptan to an enamine of formula V or VI, which is hydrolyzed to give citronellal or hydroxycitronellal. The mercaptan as the catalyst is, e.g., an aromatic mercaptan such as thiophenol or alkyldithiol and the amount is 0.5W 20wt% of the starting material. The mercaptan is, after the reaction, readily separated by washing with an aqueous alkali or distillation and reused. The use of a solvent such as alcohol in the reaction increases the selectivity of the isomerization.
SUZUKI HIDEO
YAMADA SHIN
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