Patent ID: 7737306

Claim:
A method for synthesizing a (Z,Z)-11,13-hexadecadien-1-al consisting of the following steps: reacting a starting material 10-chlorodecan-1-ol with 2,2,6,6-tetramethylpiperidinyloxy in the presence of sodium bromide, sodium acetate and sodium hypochlorite in water and ethyl acetate to form a 10-chlorodecanal; reacting the 10-chlorodecanal with triethylorthoformate in the presence of paratoluene sulfonic acid in ethyl acetate to form a 10-chloro-1,1-diethoxydecane; optionally reacting a 2,4-hexadiyne with sodium amide in the presence of diethyl ether to form a 1,3-hexadiyne; reacting a 1,3-hexadiyne with the 10-chloro-1,1-diethoxydecane, in the presence of sodium amide and diethyl ether to form a 16,16-diethoxyhexadeca-3,5-diyne; and reacting the 16,16-diethoxyhexadeca-3,5-diyne with cyclohexene and borane-N,N-diethylaniline complex in THF, acetic acid, and a reagent selected from the group consisting of sulfuric acid, copper (II) tetrafluoroborate and sodium borofluoride to form the (Z,Z)-11,13-hexadecadien-1-al.