4-Hydroxybenzophenone → 4-[Phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Participants

Reaction Steps

The McMurry procedure described for 9 (example 5, step 1) was utilized using (4-hydroxyphenyl)(phenyl)methanone (2.97 g, 14.9 mmol), 3,3,5,5-tetramethylcyclohexanone (6.25 g, 44.9 mmol), Zn (9.69 g, 149 mmol), TiCl4.2THF complex (25 g, 7.5 mmol), and THF (200 mL). Standard work-up followed by purification gave 4.50 g (91%) of the title product 32 as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 7.04 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.4 Hz, 2H), 1.98 (s, 2H), 1.95 (s, 2H), 1.28 (s, 2H), 0.93 (s, 6H), 0.92 (s, 6H).

Provenance & Evidence