Sodium Chloride → HCID 22989717, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of 3-methoxyphenol (2.00 g, 16.11 mmol) in DMF (10 mL) was slowly added over 5 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.70 g of an 80% dispersion in mineral oil, 23.33 mmol) in DMF (15 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1 h. To this slurry was added drop-wise over 5 min, 1-chloro-3-iodopropane (3.95 g, 19.32 mmol), and the resulting brown mixture was stirred at ambient temperature for 4 h. Cold water (25 mL) was carefully added, followed by saturated NaCl solution (25 mL). The resulting mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered, concentrated by rotary evaporation to a residue that was dried briefly under high vacuum producing a light-brown oil (3.27 g, quantitative yield).

Provenance & Evidence