Sulfuric Acid → 4-Prop-2-ynylcyclohexanecarboxylic acid

Participants

Reaction Steps

A solution of chromium trioxide (1.1 g, 11 mmol) in 1.5 M sulfuric acid (40 mL, 27 mmol) was maintained at 0° C. while 5.3 (0.46 g, 3 mmol) in 80 mL of acetone was added over 2 hours. The reaction was then stirred for an additional 2 hours at room temperature. The reaction mixture was diluted with ether (200 mL) and extracted 2 times with water. The organics were dried with sodium sulfate. The solvent was removed under reduced pressure and the product was purified by chromatography on silica gel column eluting with acetone-dichloromethane (70:30) to give 5.4 (75%). 1H NMR (300 MHz, CDCl3) δ 2.24 (dt, J=3.66, 12.1 Hz, 1 H), 2.10 (dd, J=2.7, 6.5 Hz, 2 H), 2.04-1.89 (m, 5 H), 1.76 (d, J=2.3 Hz, 1 H), 1.43 (dq, J=3.28, 13.1 Hz, 2 H), 1.03 (dq, J=3.28, 13.1 Hz, 2 H). 13C NMR (300 MHz, CDCl3) δ 183.2, 83.3, 69.9, 43.4, 36.7, 31.8, 28.9, 26.3.

Provenance & Evidence