p-Toluenesulfonic acid → 3-(2-Hydroxyethyl)cyclopentan-1-one

Participants

Reaction Steps

A solution of 2-(3,3-dimethoxycyclopentyl)ethanol (203.3 g, 1167 mmol), in Et2O (1000 mL) was treated with p-toluene sulfonic acid (6.66 g, 35.0 mmol) and stirred for 16 hrs. The solution was extracted with water (4×100 mL) and the combined extracts were concentrated under reduced pressure to give the title compound (142.33 g, 1110 mmol, 95% yield), as a dark brown oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.64-3.76 (2 H, m), 2.41 (1 H, dd, J=17.85, 7.17 Hz), 2.24-2.35 (2 H, m), 2.13-2.23 (2 H, m), 1.82 (1 H, dd, J=18.01, 10.38 Hz), 1.64-1.77 (2 H, m), 1.49-1.60 (1 H, m). 13C NMR (126 MHz, CDCl3) δ ppm 219.75, 61.30, 45.21, 38.54, 38.41, 34.01, 29.67.

Provenance & Evidence