[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])CCC.[CH3:24][S:25]SC.C(OCC)C>C1(C)C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C.CN(C)CCN(C)C>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([O:15][CH2:16][O:17][CH3:18])[C:3]([O:2][CH3:1])=[C:8]([S:25][CH3:24])[C:7]=1[O:9][CH2:10][O:11][CH3:12]259 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in a mixed solvent of 12 ml of toluene with 3 ml of hexamethylphosphoric triamide, and further 0.303 ml of N,N,N',N'-tetramethylethylenediamine was added thereto, and the mixture was cooled to -78° C. on a dry ice-acetone mixture bath. 1.34 Milliliters of n-butyllithium (1.6 M, n-hexane solution) was added dropwise to the reaction mixture and stirred for 20 minutes. Then 0.14 ml of dimethyl disulfide was added dropwise thereto, and reacted for additional 2 hours with stirring. The reaction mixture was warmed until room temperature, then 30 ml of diethyl ether was added thereto, and the organic layer was washed three times with 20 ml of water, then washed three times with 20 ml of a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The diethyl ether extract was concentrated under a reduce pressure, the residue obtained was purified by means of a thin layer chromatography (thickness: 2 mm, adsorbent: silica gel, developing solvent: 40%-ethyl acetate-n-hexane). There was obtained 152 mg of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-methylthiobenzene. Colorless oily substance.
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