Cyclohexanone → Methyl 4-[cyclohexylidene(4-hydroxyphenyl)methyl]benzoate

Participants

Reaction Steps

To a 3-necked round-bottomed flask were added zinc powder (0.40 g, 6.12 mmoL) and anhydrous THF (15 mL). To the stirred suspension was slowly added by syringe TiCl4 (0.32 mL, 0.55 g, 2.9 mmoL) at RT under a nitrogen atmosphere. The reaction mixture was heated at reflux for 2 h. A solution of cyclohexanone (0.24 mL, 0.227 g, 2.3 mmoL) and methyl 4-[(4-hydroxyphenyl)carbonyl]benzoate (24) (0.20 g, 0.78 mmoL) in anhydrous THF (5 mL) was added to the reaction mixture. The reaction mixture was heated a reflux for 2 h. The oil bath was removed and the reaction mixture was allowed to cool at RT. To the reaction mixture was added H2O (5 mL) followed by 10% K2CO3 (5 mL). The quenched reaction mixture was filtered through a pad of Celite with the aid of H2O and EtOAc. The filtrate was transferred to a separatory funnel and the layers were separated. The organic phase was dried (MgSO4), filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography on silica gel with a CH2Cl2:MeOH gradient (100:0 to 95:5) to give 0.176 g (70%) of compound 156 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.53 (m, 6 H), 2.10 (m, 2 H), 2.17 (m, 2 H), 3.80 (s, 3 H), 6.66 (d, J=8.3 Hz, 2 H), 6.84 (d, J=8.2 Hz, 2 H), 7.17 (d, J=8.1 Hz, 2 H), 7.86 (d, J=7.8 Hz, 2 H), 9.34 (s, 1 H).

Provenance & Evidence