Methyl iodide → 3-Hydroxy-2-methoxybenzaldehyde

To a solution of 2,3-dihydroxybenzaldehyde (20.0 g) in dimethylsulfoxide (80 ml) was added sodium hydride (5.79 g), and the mixture was stirred at room temperature for 1 hr. Methyl iodide (9.0 ml) was added, and the mixture was further stirred at room temperature for 20 hrs. The obtained reaction mixture was partitioned between ethyl acetate (1000 ml) and water (500 ml). The aqueous layer was further extracted with ethyl acetate (1000 ml). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and crystallized from diisopropyl ether and hexane to give 3-hydroxy-2-methoxybenzaldehyde (11.5 g) as pale-brown crystals.

1. stirringthe mixture was further stirred at room temperature for 20 hrs
2. customThe obtained reaction mixture
3. customwas partitioned between ethyl acetate (1000 ml) and water (500 ml)
4. extractionThe aqueous layer was further extracted with ethyl acetate (1000 ml)
5. washwashed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel chromatography
9. customcrystallized from diisopropyl ether and hexane

ORD record

ord-82786a93c6c44c2d8fa570b1593b1101

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625887B2