Phenol → Phenyl pent-4-enoate

Participants

Reaction Conditions

Reaction Steps

A 250-mL round-bottom flask equipped with a stir bar was charged with 4-pentenoic acid (5.10 mL, 50.0 mmol) and CH2Cl2 (40 mL), followed by thionyl chloride (4.00 mL, 55.0 mmol). The mixture was allowed to stir for 30 min, at which point phenol (9.45 g, 100 mmol) was added as a solution in CH2Cl2 (10 mL). The mixture was allowed to cool to 0° C. (ice-bath), and triethylamine (28 mL, 200 mmol) was added dropwise by a syringe over 5 min (N.B., strong exotherm). The resulting solution was allowed to stir for 12 h at 22° C. The reaction was quenched by addition of a saturated aqueous solution of NaHCO3 (100 mL). The organic layer was separated, and the aqueous layer washed with CH2Cl2 (5×50 mL). The combined organic layers were washed with water (1×50 mL), brine (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography (95:5 hexanes:EtOAc) to deliver a colorless oil. The oil was distilled from CaH2 under reduced pressure (1.0 torr) to afford phenyl(4-pentenoate) (2.58 g, 14.6 mmol, 29.0% yield) as a colorless oil. Spectral data matched those in the literature.

Provenance & Evidence