3-Hydroxybenzophenone → HCID 69518274, compound

Participants

Reaction Steps

To a solution of (3-hydroxyphenyl)(phenyl)methanone (30.0 g, 151 mmole) in anhydrous THF (300 mL) at 0° C. was slowly added a solution of potassium-t-butoxide (200 mL-1 M in THF, 0.200 mmole), followed by a slow addition of [2-(chloromethoxy)ethyl](trimethyl)silane (32.1 mL, 182 mmole). After stirring the mixture for 2 h, the solvent was removed in vacuo and the residue redissolved in a mixture of H2O (200 mL) and EtOAc (200 mL). The aqueous layer was further extracted with EtOAc (2×100 mL). The combined extracts were washed with H2O (200 mL), 0.1 N HCl (500 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give an orange oil. The crude product was redissolved in hexanes and filtered through a silica-gel plug to give the product as an impure pale yellow oil which is carried on without further purification: ESHRMS m/z 329.1586 (M+H, C19H25O3Si, Calc'd 329.1567).

Provenance & Evidence