Hydrochloric Acid → HCID 68501670, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of Zn dust (3.76 g, 57.5 mmol), 3,3,5,5-tetramethyl cyclohexanone (2.95 g, 19.2 mmol), 4-bromobenzophenone (5.00 g, 19.15 mmol) and anhydrous THF (100 mL) under N2 was cooled to −10° C. and a 1 M solution of TiCl4 in toluene (30 mL) added, dropwise, over 10 min. The temperature was maintained below 0° C. during the addition. After addition was complete the reaction was allowed to warm to RT and then heated at 90° C. for 2 h. The reaction was cooled to −10° C. and concentrated HCl (15 mL) added dropwise followed by water (15 mL). After stirring 30 min, EtOAc (100 mL) was added and the pale yellow 2-phase mixture washed with water (2×75 mL) and brine (1×75 mL) then dried (MgSO4) and concentrated to 8.26 g of a pale yellow oil. The crude oil is purified by column chromatography on 250 g silica gel with 2% EtOAc/hexanes to afford 4.17 g (58%) of the title compound (16) as a white solid. 1H-NMR indicated that the product (16) was contaminated with ˜8% of an impurity consistent with the pinacol intermediate formed during the McMurry reaction. 1H NMR (400 MHz, DMSO-d6): δ7.46 (d, J=8.3 Hz, 2H), 7.28 (t, J=7.5 Hz, 2H), 7.04-7.19 (m, 5H), 1.87 (s, 4H), 1.24 (s, 2H), 0.87 (s, 6H), 0.86 (s, 6H).

Provenance & Evidence