3-Bromophenol → 2-(3-Bromophenoxy)-2-methylpropanal

関与物質

反応手順

Cetyltrimethyl ammonium bromide (0.28 g, 0.77 mmol) was added to a solution of 3-bromophenol (6.66 g, 38.5 mmol) in 3.85M aqueous sodium hydroxide solution (10 ml), followed by a solution of 1,1-dichloro-2-hydroxy-2-methylpropane (A) (1.37 g, 9.6 mmol) in ether (20 ml). The mixture was stirred under an argon atmosphere for 18 hours then diluted with ether (50 ml), and extracted with 2M aqueous sodium hydroxide solution (4×30 ml), to remove unreacted phenol. The combined aqueous extracts were extracted with ether (50 ml), and the organic phase was washed with 2M aqueous sodium hydroxide solution (20 ml) followed by water (50 ml). The combined organic extracts were dried (MgSO4), concentrated, and purified by flash column chromatography, eluting with ethyl acetate/hexane (1:10 v/v), to give 2-(3-bromophenoxy)-2-methylpropanal (0.89 g), as an oil; NMR: 1.45(6H,s), 6.75-7.20(4H,m), 9.8(1H,s).

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