Hydrochloric Acid → (4-Oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

Participants

Reaction Steps

To a solution of (4,4-dimethoxycyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (5.4 g, 10.53 mmol) in THF (20 mL) was added 1 N aq HCl (60 mL, 60.0 mmol) and the reaction mixture was refluxed for 3 h. Volatiles were removed in vacuo, and the aqueous layer was extracted with EtOAc (5×10 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (4.3 g, 87% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.78 (d, J=8.3 Hz, 4H), 7.39 (d, J=8.0 Hz, 4H), 3.97 (s, 4H), 2.50 (s, 6H), 2.25 (t, J=7.0 Hz, 4H), 1.75 (t, J=7.0 Hz, 4H).

Provenance & Evidence