Water → HCID 66842949, compound

Participants

Reaction Steps

To 5-(2-Phenylethenyl)-2-1-propyl-1,3-benzenediol obtained in Example 11 (1.00 g, 3.93 mmol) and triethylamine (1.5 mL, 10.8 mmol) in dichloromethane (100 mL) at 0° C. was added acetyl chloride dropwise. The reaction was monitored by TLC. Water (50 mL) was added after the reaction was complete (−30 min.). The organic layer was separated and washed with 2NHCl (30 mL), H2O (50 mL), saturated NaHCO3 (50 mL), H2O (50 mL) and brine (50 mL), and dried over anhydrous sodium sulfate. Evaporation of the solution followed by flash chromatography using 5% ethyl acetate in hexane yielded 3-acetoxy-5-(2-phenylethenyl)-2-1-propylphenyl acetate. (1.32 g, 92%) as a white solid. 1HNMR (CDCl3, ppm): δ 1.26 (d, J=7.0 Hz, 6H), 2.35 (s, 6H), 3.08 (hept., J=7.0 Hz, 1H), 6.98 (d, J=17.4 Hz, 1H), 7.04 (d, J=17.4 Hz, 1H), 7.07 (s, 2H), 7.24-7.29 (m, 1H), 7.34-7.38 (m, 2H), 7.45-7.49 (m, 2H).

Provenance & Evidence