OO.C([OH:7])(C)(C)C.C=CCCCCC.[O:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18][OH:19])O>[W].C(OC)(C)(C)C>[O:19]([CH2:18][CH:17]([OH:15])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[OH:7]To a 50 mL flask equipped with a magnetic stirrer and a reflux condenser were added 800 mg of the tungsten-containing mesoporous silicate prepared in Example 1, 800 mg of a 60% by weight aqueous hydrogen peroxide solution, 2 g of tert-butanol and 400 mg of 1-heptene, and the mixture was stirred and maintained at an inner temperature of 40° C. for 16 hours to react these materials. To the resulting reaction mixture was added 5 g of methyl tert-butyl ether, and the mixture was stirred, and then allowed to stand. The supernatant organic layer was analyzed by LC, and it was found that 2-hydroperoxy-l-hydroxyheptane and 1-hydroperoxy-2-hydroxyheptane were produced. When the organic layer was analyzed by GC, 2-hydroperoxy-1-hydroxyheptane and 1-hydroperoxy-2-hydroxyheptane were thermally decomposed at an injection inlet, and detected as 1-hexanal. Then, the yield of 1-hexanal was determined by GC analysis (internal standard method), and this was regarded as the yield of 2-hydroperoxy-1-hydroxyheptane and 1-hydroperoxy-2-hydroxyheptane. Yield: 22%. The recovery of 1-hexene was 67%.
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