Vanillin → 4-Methoxy-3-[(prop-2-yn-1-yl)oxy]benzaldehyde

Temperature

80 °C

A mixture of vanillin 17 (0.76 g, 4.90 mmol), K2CO3 (1.37 g, 9.90 mmol) and propargyl bromide (1.19 g, 6.90 mmol) in DMF (30 mL) was refluxed at 80° C. for 1 hr. Reaction mixture was cooled to 0° C. in ice bath and filtered through a short bed of celite. Ethyl acetate (50 mL) was added and the mixture was washed with 1N HCl (20 mL), extracted with ethyl acetate (100 mL). The organic phase was combined and washed with brine and dried over anhydrous Na2SO4. After filtration, solvent was removed under reduced pressure and the crude residue was purified by flash chromatography (hexane/ethyl acetate: 8/2) to afford 18 as white solid (0.74 g, 80%). 1HNMR (400 MHz, CDCl3) δ 2.57 (t, 1H), 3.94 (s, 3H), 4.85-4.86 (d, J=2.44 Hz, 2H), 7.13-7.15 (d, J=8.16 Hz, 1H), 7.43-7.47 (m, 2H), 9.87 (s, 1H); 13CNMR (100 MHz, CDCl3) δ 56.06, 56.65, 109.58, 112.71, 126.21, 131.00, 150.11, 152.17, 190.85.

1. customReaction mixture
2. temperaturewas cooled to 0° C. in ice bath
3. filtrationfiltered through a short bed of celite
4. additionEthyl acetate (50 mL) was added
5. washthe mixture was washed with 1N HCl (20 mL)
6. extractionextracted with ethyl acetate (100 mL)
7. washwashed with brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationAfter filtration, solvent
10. customwas removed under reduced pressure
11. customthe crude residue was purified by flash chromatography (hexane/ethyl acetate: 8/2)

ORD record

ord-e455882f362243c08dd1e181c981191f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260473B2