Formaldehyde → 3-Hydroxy-5-methoxybenzaldehyde

Temperature

0 °C

To a solution of 60% sodium hydride (2.77 g, 69.3 mmol) in N,N-dimethylformamide (50 ml) was gradually added at 0° C. ethanethiol (7 ml), and the solution was stirred at 0° C. for 30 minutes, followed by refluxing under heating for 1 hour. The mixture was cooled to room temperature, and thereto was added 3,5-dimethoxybenzaldehyde (3.84 g, 23.1 mmol) in N,N-dimethylformamide (90 ml) and the mixture was refluxed under heating for 1 hour. The mixture was cooled to room temperature, and thereto were added a saturated aqueous sodium chloride solution (700 ml), 26% aqueous formalin solution (70 ml) and acetic acid (130 ml) in the order. The mixture was stirred, extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography. (hexane:ethyl acetate=2:1) to give the subject compound (2.68 g, 17.6%).

1. temperatureby refluxing
2. temperatureunder heating for 1 hour
3. temperatureThe mixture was cooled to room temperature
4. temperaturethe mixture was refluxed
5. temperatureunder heating for 1 hour
6. temperatureThe mixture was cooled to room temperature
7. stirringThe mixture was stirred
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with water
10. dry with materialan aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate
11. customThe solvent was removed under reduced pressure
12. customthe residue was purified with silica gel chromatography

ORD record

ord-87efabde2b0644769ba37fa8075e281a

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220773B2