Allyl bromide → 2-Allyloxy4-(benzyloxy)benzaldehyde

Beteiligte Stoffe

Reaktionsschritte

A solution of 45.8 g (0.20 mole) 2-hydroxy-4-(benzyloxy)benzaldehyde in 250 mL of dimethylformamide was added dropwise over 1 hour to a slurry of 10.6 g (0.26 mole) of 60% sodium hydride/mineral oil dispersion in 100 mL of dimethylformamide. The mixture was stirred under nitrogen for 1 hour at room temperature, and then 28 mL (0.33 mole) of allyl bromide in 30 mL of dimethylformamide was added. The reaction was heated at 60° C. for 4 hours under nitrogen. The solvent was then removed in vacuum and replaced with 500 mL of ethyl acetate. This solution was washed with 500 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum to give 53.6 g (100%) of the title compounds as a pale yellow solid. 1H-NMR (d6-DMSO): singlet 10.2 δ (1H); doublet of doublets 7.65 δ (1H); multiplet 7.40 δ (5H); doublet 6.80 δ (1H); doublet of doublets 6.75 δ (1H); multiplet 6.05 δ (1H); doublet of doublets 5.45 δ (1H); doublet of doublets 5.30 δ (1H); singlet 5.20 δ (2H); multiplet 4.70 δ (2H).

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