Hydrochloric Acid → 1-[4-(6-{[Tert-butyl(dimethyl)silyl]oxy}hexyl)phenyl]-3-chloropropan-1-one

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tert-Butyl(dimethyl)[(6-phenylhexyl)oxy]silane (21.00 g), 3-chlorophenylpropionyl chloride (9.14 g) and CS2 solvent (100 mL) were placed in a two neck flask equipped with a reflux condenser. The mixture was then cooled to −78° C. and AlCl3 (19.20 g) was added. The reaction mixture was stirred at −78° C. for 15 min., followed by: 0° C. for 20 min., 25° C. for 30 min., 40° C. for 40 min., 25° C. for 14 h. During the course of the temperature ramping, gas evolution (presumably HCl) was noted. The reaction was then quenched with several portions of 100 mL water/30 mL conc. HCl and the resulting mixture was transferred to a separatory funnel. The organic products were extracted into chloroform (4×200 mL). The chloroform fractions were combined and dried over MgSO4. The solvent was then removed by roto-evaporation to give a tan oil which solidified on standing overnight. 1H NMR shows the presence of resonances consistent with the desired product.

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