Potassium Carbonate → 4-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Participants

Reaction Steps

To a stirred suspension of zinc powder (23.4 g, 0.36 mol) in THF (300 mL) was slowly added TiCl4 (20 mL, 0.18 mol) via a syringe at room temperature under a nitrogen atmosphere. The reaction mixture was heated at reflux for 1 h. A solution of (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (10.0 g, 0.036 mol) and 3,3,5,5-tetramethylcyclohexanone (16.7 g, 0.108 mol) in THF (100 mL) was added to the reaction mixture. The reaction mixture was heated at reflux with stirring under a nitrogen atmosphere for an additional 2 h. The reaction mixture was allowed to cool to room temperature. To the reaction mixture was poured into a 10% aqueous K2CO3 (1 L). The reaction mixture was filtered through a pad of Celite and the pad washed with EtOAc. The filtrate was transferred to a separatory funnel and the layers were separated. The aqueous phase was further extracted with EtOAc (4×250 mL). The combined organic phase washed with brine (2×10 mL), dried (Na2SO4), filtered, and then filtrate was concentrated under reduced pressure to give the crude product as a gold-yellow oil. The crude product was purified by flash chromatography on silica gel with hexanes:EtOAc (100:0 to 1:1) as an eluent to afford 10.45 g (73%) of compound 14 as a white solid. 1H NMR (300 MHz, CDCl3): δ 0.91 (s, 6 H), 0.95 (s, 6H), 1.31 (s, 2 H), 1.96 (s, 2 H), 1.99 (s, 2 H), 4.67 (s, 1H), 6.76 (d, J=8.7 Hz, 2 H), 7.03 (d, J=6.0 Hz, 2 H), 7.05 (d, J=6.0 Hz, 2 H), 7.41 (d, J=8.4 Hz, 2 H). HRMS (EI) Calcd for C23 H27BrO: 398.1245 (M+). Found: 398.1248.

Provenance & Evidence