Benzyl Bromide → 2-(Benzyloxy)-3-hydroxybenzaldehyde

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Reaction Steps

For example, sodium hydride (0.52 g, 21.7 mmol) is added to DMSO (20 ml) followed by an aldehyde of formula 11 wherein R3, R4 and R5 are hydrogen, i.e., 2,3-dihydroxybenzaldehyde, (2.8 g, 20.2 mmol). After stirring the solution for 1 h at ambient temperature, benzyl bromide 12 (2.4 ml, 20.2 mmol) was added forming a red-brown reaction mixture which was further stirred 12 h at ambient temperature. The solution was then partitioned between ethyl acetate (200 ml) and 0.5 N hydrochloric acid (300 ml). The organic layer was separated and MgSO4, filtered and concentrated to afford a brown oil. The brown oil is purified by flash chromatography (15% ethyl acetate/hexane) to give 3.21 g of 2-benzyloxy-3-hydroxy-benzaldehyde 16.

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