Methanol → (2E)-3-(2,6-dimethoxyphenyl)acrylaldehyde

Temperature

0 °C

Add 355 mL of a 1M solution of diisobutylaluminium hydride (DIBAL-H) (355 mmol) in toluene to a solution of 61 g (322 mmol) of (2E)-3-(2,6-dimethoxyphenyl)acrylonitrile in 600 mL of anhydrous toluene under argon and cooled to 0° C., maintaining the temperature at 0° C. Then bring the reaction mixture to room temperature (RT) and stir for 3 h. Then add 13 mL (322 mmol) of methanol and then, dropwise, 170 g (174 mmol) of an aqueous solution of sulphuric acid at 10 wt. %. Stir the suspension for one hour, then filter on a celite bed. Wash the filtrate with 500 mL of water then dry over Na2SO4 and concentrate under reduced pressure. Take up the residue obtained in 500 mL of DCM and filter in a silica column, eluting with DCM. After concentration under reduced pressure, we obtain 37 g of (2E)-3-(2,6-dimethoxyphenyl)acrylaldehyde in the form of colourless oil.

1. temperaturemaintaining the temperature at 0° C
2. customto room temperature
3. custom(RT)
4. stirringStir the suspension for one hour
5. filtrationfilter on a celite bed
6. washWash the filtrate with 500 mL of water
7. dry with materialthen dry over Na2SO4
8. concentrationconcentrate under reduced pressure
9. customobtained in 500 mL of DCM
10. filtrationfilter in a silica column
11. washeluting with DCM
12. concentrationAfter concentration under reduced pressure, we

ORD record

ord-088b344ef0ad49559dc9a20036affd12

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552201B2