Citral (3,7-dimethyl-2,6-octadienal, 1) occurs in lemongrass, cubeb, citrus, and other essential oils as a mixture of the E-and Z-isomers in a 7:3 ratio. This aldehyde (1) has a strong lemon odor [1] and is used widely in many perfume compositions.The goal of our work was to develop preparative synthetic methods of citral oxime esters through the reaction of citral oxime (2) with alkylcarboxylic acid anhydrides or alkyl-and arylcarboxylic acid chlorides in the presence of pyridine. The synthesis was performed at 20-23°C for 24-36 h by simply mixing the appropriate reagents and proceeded without using cooling and prolonged stirring. Citral oxime esters 3-22 were prepared in 74-88% yield.
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