Hydrochloric Acid → 4-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone

Participants

Reaction Steps

To a well-stirred mixture of β-ionone (10.00 g, 52.1 mmol) and DBU (79 mg, 0.52 mmol (1 mol-%)) was rapidly added 3-mercaptopropyltrimethoxysilane (10.21 g, 52.1 mmol) at 25-30° C. After 72 hours, the reaction mixture was poured onto a cold stirred 5% aqueous HCl solution and extracted twice with Et2O. The organic phases were washed (H2O, saturated aqueous NaHCO3 and brine), dried (Na2SO4), filtered and concentrated. The crude extract was dried for 1 hour at 65-70° C./0.01 Torr to give 18.00 g of the title thioether containing approximativaly 10% of β-ionone. Yield: 80%.

Provenance & Evidence