Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

##STR00001##

Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

##STR00001##

Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

##STR00001##

Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether (1) to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol (2), and a method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate comprising a step of acetylating the produced 2,6-dimethyl-1,5-heptadien-3-ol (2) to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate (3). ##STR00001##

Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether (1) to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol (2), and a method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate comprising a step of acetylating the produced 2,6-dimethyl-1,5-heptadien-3-ol (2) to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate (3). ##STR00001##

Provided herein are reactor systems and processes for producing organic acids directly from beta-lactones. Such reactor systems and processes involve the use of a heterogeneous catalyst, such as a zeolite at vapor phase conditions. The reactor systems and processes may use a fixed bed, moving bed or fluidized contacting zone as reactor configurations.

Provided herein are reactor systems and processes for producing organic acids directly from beta-lactones. Such reactor systems and processes involve the use of a heterogeneous catalyst, such as a zeolite at vapor phase conditions. The reactor systems and processes may use a fixed bed, moving bed or fluidized contacting zone as reactor configurations.

Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3). ##STR00001##

Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3). ##STR00001##

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities' options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.