3-Hydroxybenzaldehyde → 3-(1-Propenyl)phenol

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To a suspension of (ethyl)triphenylphosphonium bromide (35 g, 94.3 mmol) in THF (95 mL) was added potassium bis (trimethylsilyl)amide (180 ml, 0.5M in toluene, 90.2 mmol) dropwise. The reaction was stirred at 0° C. for 30 min, then a solution of 3-hydroxy-benzaldehyde (5 g, 41.0 mmol) in THF (5 mL) was added dropwise. After addition the reaction was stirred at 0° C. for 1 h. Ethyl ether (200 mL) was added to dilute the reaction. The organic layer was washed with water (50 mL×2), brine (50 mL×2) and dried over magnesium sulfate. Purification was performed by flash chromatography on 600 g silica gel, loaded and eluted with 10% ethyl acetate in hexane. Pure fractions were combined and evaporated to give the title compound (5.1 g, 93%) as a colorless oil.

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