3,3,5,5-Tetramethylcyclohexanone → 4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

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Reaction Steps

The coupling procedure described for 1 (example 1, step 1) was employed. A mixture of (4-fluorophenyl)(4-hydroxyphenyl)methanone (4.32 g, 20 mmol), 3,3,5,5-tetramethylcyclohexanone (9.26 g, 60 mmol), Zn (13 g, 200 mmol), TiCl4 (10.9 mL, 100 mmol), and THF (400 mL) was refluxed for 2.5 h. Standard work-up followed by purification afforded 5.450 g (80%) of the title product 9 as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.15-7.11 (m, 2H), 7.04 (d, J=8.7 Hz, 2H), 7.00-6.94 (m, 1H), 6.76 (d, J=8.7 Hz, 2H), 4.68 (br s, 1H), 2.0 (s, 2H), 1.96 (s, 2H), 1.31 (s, 2H), 0.95 (s, 6H), 0.94 (s, 6H). LCMS (APCI): m/z 429 (M+H)+.

Provenance & Evidence