4-Methoxyphenol → 2-(4-Methoxyphenoxy)-2-methylpropanal

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A solution of 4-methoxyphenol, (21.72 g, 0.175 mol), in aqueous sodium hydroxide solution, (5.8M, 30 ml), was treated with cetyltrimethyl ammonium bromide, (0.255 g, 0.7 mmol), followed by a solution of 1,1-dichloro-2-hydroxy-2-methylpropane, (5.01 g, 35 mmol), in ether, (70 ml). The mixture was stirred under an argon atmosphere for 18 hours then diluted with ether, (100 ml), and extracted with aqueous sodium hydroxide solution, (2M, 4×50 ml), to remove unreacted phenol. The combined aqueous extracts were extracted with ether, (100 ml), and the organic phase was washed with aqueous sodium hydroxide solution, (2M, 50 ml), and water, (100 ml). The combined organic extracts were dried, (MgSO4), concentrated and purified by flash column chromatography, eluting with ethyl acetate/hexane, (10%, v/v), to give 2-(4-methoxyphenoxy)-2-methylpropanal, (3.61 g), as an oil; NMR: 1.36(6H,s), 3.76(3H,s), 6.7-6.9(4 H,m) and 9.85(1H,s).

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