CO[C:3]1[C:8](OCOC)=[CH:7][C:6](OC)=[C:5](OCOC)[C:4]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C#CCCCC.C(#N)C.O.O[Si](O)=O>CO.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.N1C2C(=CC=CC=2)C=CC=1>[CH3:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:4]=[CH:3][CH2:8][CH2:7][CH2:6][CH3:5]1 Gram of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]tridec-8-yne prepared in the above-mentioned (2) was dissolved in 10 ml of methanol, to this solution was added 40 mg of 5%-palladium-barium sulfate-quinoline (1:1) and the mixture was catalytically reduced under a normal hydrogen pressure at room temperature for 4 hours. This reaction was traced by means of a high performance liquid chromatography. Thus, the reaction was determined by measuring the optical density (OD) at UV254 under conditions of ODS column, 80%-acetonitrile-water, 2 ml/minute. After the reaction was completed, the catalyst was removed by filtration, and methanol was removed by evaporation under reduced pressure, and the residue obtained was treated by means of a column chromatography ("Robar " column, LiChrosorb RP-8, Type C, manufactured by E. Merck A. G.) and eluted with 75%-acetonitrile-water at the flow rate of 5 ml/minute to obtain both Z-isomer and E-isomer, respectively. There was obtained 0.65 g of 1-[2,5-dimethoxy-3,6-bis-Imethoxymethoxy)phenyl]tridec-8 -ene (Z-isomer) as in the form of colorless oily substance.
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