Triphenylphosphine → HCID 178459243, Verbindung

A mixture of 1.994 grams (11.57 mmol) of trans-p-menthane-7,8diol (for preparation, see: Ohloff, G.; Giersch, W. Helv. Chim. Acta., 1980, 63, 76), 3.035 grams (11.57 mmol) of triphenylphosphine, and 20 mL of benzene was chilled in an ice bath and treated portionwise with 2.060 grams (11.57 mmol) of N-bromosuccinimide. The ice bath was removed and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with 50 mL of hexane and the solids were removed by filtering sequentially through celite and filter paper. The filtrate was washed with 0.5 Na2S2O3 solution (2×100 mL), 1 N sodium hydroxide solution (1×50 mL), brine (1×50 mL), dried (Na2SO4), and evaporated. The residue was diluted with hexane and filtered to remove triphenylphospineoxide. The residue was purified by flash chromatography using a 10-50% EtOAc-hexane eluant to give 3.382 grams (88%) of the title compound an oil. 1H NMR (CDCl3) d 0.93-1.28 (6H, m), 1.15 (6H, s), 1.58 (1H, br s), 1.83-2.00 (4H, m), 3.27 (2H, d, J=7 Hz).