Vanillin → 4-[(6-Hydroxyhexyl)oxy]-3-methoxybenzaldehyde

A flame-dried, 100 mL round bottom flask equipped with a claisen arm and reflux condenser was charged, under argon, with vanillin (1, 1.0 g, 6.6 mmol), tetrabutylammonium iodide (369 mg, 1 mmol), and potassium carbonate (1.38 g, 10 mmol). These were suspended in 10 mL of anhydrous acetonitrile and then 6-chlorohexanol (1.05 ml, 7.9 mmol) was added dropwise. The reaction was protected from light and refluxed for 15 hours at which time TLC analysis showed complete consumption of the starting material. The solvent was evaporated in vacuo and the residue was then dissolved in 50 mL of ethyl acetate and extracted with water (2×100 mL), brine (1×100 mL), and water (1×100 mL). The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo to give 1.5 g (90%) of 2 as a white solid. Rf=0.29 (33% ethyl acetate/hexane). Mp 55.0-56.0° C. 1H NMR (400 MHz, DMSO-d6): δ9.83 (s, 1), 7.53 (dd, J=2.0 Hz, 8.0 Hz, 1), 7.39 (d, J=2.0 Hz, 1), 7.17 (d, J=8.4 Hz, 1), 4.36 (t, J=5.2 Hz, 1), 4.07 (pt, J=2.4 Hz, 2.8 Hz, 2), 3.83 (s, 3), 3.39 (dd, J=5.6 Hz, 11.6 Hz, 2), 1.75 (m, 2), 1.45-1.34 (m, 6) ppm.

1. customA flame-dried, 100 mL round bottom flask equipped with a claisen arm
2. temperaturereflux condenser
3. temperaturerefluxed for 15 hours at which time TLC analysis
4. customconsumption of the starting material
5. customThe solvent was evaporated in vacuo
6. dissolutionthe residue was then dissolved in 50 mL of ethyl acetate
7. extractionextracted with water (2×100 mL), brine (1×100 mL), and water (1×100 mL)
8. dry with materialThe organic layer was dried over magnesium sulfate
9. filtrationfiltered
10. customthe solvent was evaporated in vacuo

ORD record

ord-4149157235714236bf21c1375c3dc6de

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06632641B1