[CH:1]1([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[CH3:11][O:12]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1To a mixture of (cyclopropylmethyl)benzene (1.32 g) and dichloromethyl methyl ether (1.25 ml) in dichloromethane (20 ml) was added 1.0M solution of titanium(IV) chloride in dichloromethane (15 ml) at 0° C. under nitrogen atmosphere. The mixture was stirred at 0° C. for 10 minutes, then poured into ice water. The organic layer was separated and washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (9:1) to give 4-(cyclopropylmethyl)benzaldehyde (580 mg) as an oil.
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