Hydrochloric Acid → 4-Hexyl-2-methoxy-1-phenoxybenzene

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Reaction Steps

Under nitrogen, ZnCl2 (0.5 M solution in tetrahydrofuran; 6.8 mL, 3.41 mmol) was added by syringe to a round-bottomed flask sealed with a rubber septum and purged with nitrogen. Hexyl magnesium chloride (1.0 M solution in THF; 4.0 mL, 4.26 mmol) was then added dropwise by syringe, and the resulting solution was stirred at room temperature for 20 minutes. Next, N-methylpyrrolidinone (4.7 mL) was added by syringe. After 5 minutes, 21.7 mg (0.0426 mmol) Pd(P(t-Bu)3)2 and 500 mg (2.13 mmol) of compound (3) were added. The flask was then fitted with a reflux condenser and heated under refluxed for 48 hours. The flask was then gradually cooled to room temperature, and 20 mL of a 1.0M aqueous HCl solution was added. The resulting mixture was extracted with diethyl ether and the ether extract was washed with water, then dried over anhydrous MgSO4 and concentrated under vacuum to give the crude product. Purification by flash chromatography on silica gel afforded analytically pure compound (4a): 1H NMR (300 MHz) (CDCl3): δ 7.36-6.80 (m, 8H), 3.90 (s, 3H), 2.71-2.66 (t, 2H), 1.74-1.67 (m, 2H), 1.42-1.33 (m, 6H), 1.01-0.97 (t, 3H).

Provenance & Evidence