o-Vanillin → 3-Methoxy-2-(2-methylpropoxy)benzaldehyde

A solution of 2-hydroxy-3-methoxybenzaldehyde (4.00 g, 26.2 mmol) in DMF (50 mL) was treated with K2CO3 (8.00 g, 57.9 mmol) followed by iodoisobutane (4.53 mL, 39.4 mmol). The resulting slurry was stirred for at ambient temperature for 18 h. Additional DMF (70 mL) was added to help aid stirring, and the mixture was heated to 40° C. for 18 h. Additional iodoisobutane (2.26 mL, 19.7 mmol) was added and the mixture was stirred at ambient temperature for 48 h. The reaction was quenched with H2O (100 mL) and the mixture was extracted with EtOAc (3×100 mL). The combined organics were washed with H2O (2×100 mL) and brine (2×100 mL), dried (Na2SO4) and concentrated to an orange oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 90:10) gave the title compound (2.46 g, 62%) as a clear oil: 1H NMR (300 MHz, DMSO-d6) δ 10.34 (s, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.27 (dd, J=7.8, 1.7 Hz, 1H), 7.19 (dt, J=7.8, 0.6 Hz, 1H), 3.85 (m, 5H), 2.09-2.00 (m, 1H), 0.99 (d, J=6.7 Hz, 6H).

1. stirringstirring
2. temperaturethe mixture was heated to 40° C. for 18 h
3. stirringthe mixture was stirred at ambient temperature for 48 h
4. customThe reaction was quenched with H2O (100 mL)
5. extractionthe mixture was extracted with EtOAc (3×100 mL)
6. washThe combined organics were washed with H2O (2×100 mL) and brine (2×100 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated to an orange oil
9. customPurification by column chromatography (silica gel, hexanes/EtOAc, 90:10)

ORD record

ord-cf82ad6496c241bebc179874e66a643d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2