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

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).

1. extractionextracted with aqueous sodium hydroxide solution, (2M, 4×50 ml),
2. customto remove unreacted phenol
3. extractionThe combined aqueous extracts were extracted with ether, (100 ml)
4. washthe organic phase was washed with aqueous sodium hydroxide solution, (2M, 50 ml), and water, (100 ml)
5. dry with materialThe combined organic extracts were dried, (MgSO4),
6. concentrationconcentrated
7. custompurified by flash column chromatography
8. washeluting with ethyl acetate/hexane, (10%, v/v),

ORD record

ord-90a5560f32674f5fbefba900c71ff540

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05053415