Hydrochloric Acid → (5-Iodo-3-methyl-pentyl)-benzene

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Reaction Steps

5 g (28 mmol) Phenoxanol (3-Methyl-5-phenyl-pentan-1-ol) is dissolved in 200 ml dichloromethane under nitrogen and stirring. Triphenylphosphine (8.8 g, 34 mmol) and 4.2 g (53 mmol) pyridine are added at 25° C. After cooling to 0° C. iodine (8.5 g, 34 mmol) is added. After 2 h stirring at 0° C. the reaction mixture is poured on ice-cooled 1 N HCl and extracted with dichloromethane. The combined organic phases are washed with 10% Na2S2O3, sat. NaHCO3 and sat. NaCl. Drying over MgSO4 and evaporation gives 17 g of a residue which is triturated with hexane and filtered over a 5 cm Silicagel pad. The filtrate is evaporated under reduced pressure and dried under high vacuum giving 7.1 g of 7c as a colorless oil.

Provenance & Evidence