3-Phenylprop-2-En-1-Ol → HCID 54180613, compound

Participants

Reaction Steps

To a four-neck 1000 ml round bottom flask, equipped with a mechanical stirrer, thermometer, and condenser, were added 50% w/w aqueous sodium hydroxide (“NaOH”) (250 ml), epibromohydrin (56 g, 400 mmol), and tetrabutylammoniumhydrogen sulfate (“TBAHS”) (5.2 g, 14.9 mmol). The mixture was stirred at room temperature for a period of time of about 20 minutes. To the mixture was added cinnamyl alcohol (50 g, 365 mmol), drop-wise over a period of time of about 60 minutes. The reaction was conducted at ice/water temperatures, and was allowed to continue overnight with stirring. Once the reaction was complete, the mixture was cooled and ice cold water (500 ml) was slowly added. The quenched reaction was allowed to stir for a period of time of about 30 minutes and then twice extracted with diethyl ether (250 ml). The organic portion was separated and twice washed with brine (250 ml), dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness in vacuo. Crude CGE was obtained as a clear amber liquid (67.0 g), which was distilled in vacuo (119-135° C. at 820 mTorr) to provide CGE (48.1 g, 247.8 mmol), as a clear colorless liquid. G.C. 98.0% (retention time 8.10 min.). 1H NMR (CDCl3) δ7.2-7.4 (br m, 5, C6H5), 6.65 (d, 1, —CH═), 6.25 (m, 1, ═CH—), 4.2 (br m, 2, CH2), 3.75 and 3.20 (d, 2, CH2), 3.45 (m, 1, OCH), 2.8 and 2.6 (d, 2, OCH2). FT-IR (neat) 3081, 3057, 3025, 2999, 2922, 2855, 1495, 1448, 1253, 1115, 969, 902, 855, 746, 694.

Provenance & Evidence