1-Iodopropane → 1,3,5-Trimethoxy-2-propylbenzene

To the stirred solution of 1,3,5-trimethoxybenzene (10.0 g, 59.4 mmol) in 150 mL of dry THF at 0° C. in nitrogen atmosphere was added 23.7 mL (59.3 mmol) of 2.5 M n-BuLi in hexane dropwise via syringe. The resulting solution was stirred at room temperature for 4 hr. The mixture was cooled to -20° C. and 1-iodopropane (6.09 mL, 62.5 mmol) was added dropwise via syringe in 10 min. After being stirred at room temperature for 14 hr and refluxed for 4 hr, the mixture was quenched with 200 mL of water, concentrated in vacuo to remove THF and extracted with ether. The organic layer was washed with water, dried (MgSO4) and concentrated. The crude product was washed with hexane to give 11.07 g of the title compound: mp 48.5-49.5° C.; 1H NMR (CDCl3): 6.13 (2 H, s), 3.80 (3 H, s), 3.79 (6 H, s), 2.52 (2 h, m), 1.44 (2 H, sex, J=7.5 Hz), 0.91 (3 H, t, J=7.5 Hz).

1. temperatureThe mixture was cooled to -20° C.
2. stirringAfter being stirred at room temperature for 14 hr
3. temperaturerefluxed for 4 hr
4. customthe mixture was quenched with 200 mL of water
5. concentrationconcentrated in vacuo
6. customto remove THF
7. extractionextracted with ether
8. washThe organic layer was washed with water
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. washThe crude product was washed with hexane

ORD record

ord-a0d25d40dae243dfb3b37dbcac3a7ccd

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057315