3-Phenylprop-2-En-1-Ol → Dicinnamyl ether

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 NaOH (250 ml), cinnamyl bromide (80.44 g, 400 mmol), and 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 maintaned at a temperature below about 30° C. with an ice water bath, and allowed to stir overnight. 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 dichloromethane (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 di-CE (96.0 g) was obtained as an amber liquid that was distilled in vacuo (175-180° C. at 775 mTorr) to provide distilled di-CE (75.0 g, mmol) as a clear yellow liquid. G.C. 87.1% (retention time 11.95 min.). 1H NMR (CDCl3) δ7.2-7.4 (br m, 10, C6H5), 6.65 (d, 2, CH), 6.35 (m, 2, CH), 4.2 (d, 4, CH2). FT-IR (neat) 3081, 3058, 3026, 2928, 2845, 1677, 1495, 1448, 1360, 1124, 1072, 969, 742, 693.

Provenance & Evidence