CC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:11]([OH:15])(C)(C)C.[Se](=O)=O.C1(C(C)=C)C=CC=CC=1>C(Cl)Cl.C(O)(=O)C>[OH:15][CH2:11][C:9]([C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH2:10]
A 12.5 ml of decane solution of 5 to 6 mol/L of per-tert-butylalcohol is diluted with 50 ml of methylene chloride, then 111 mg of selenium dioxide and 90.1 mg of an acetic acid were added thereto to react while stirring at room temperature for 30 min. Then, 6.5 ml of 2-phenylpropene was added to the reaction solution to react while stirring for 72 hours, followed by condensation under reduced pressure, and purification by silica gel column chromatography to obtain 3.98 g of 3-hydroxy-2-phenylpropene (yield: 59%). Measurement results by 1H-NMR and 13C-NMR of 3-hydroxy-2-phenylpropene obtained are shown below.
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