Dimethylformamide → 3-Ethoxy-4-methoxybenzaldehyde

To a 500 ml three-neck flask equipped with a mechanical stirrer and an inert gas tube were added 30.5 g of isovanillin, 55.2 g of potassium carbonate, 49.9 g of iodoethane and 140 ml of DMF. The mixture was stirred overnight at the room temperature. The mixture was poured into 1400 ml of water, and then the resultant mixture was extracted with ethyl acetate (600 ml×2). The ethyl acetate layers were combined. The organic phase was washed with saturated Na2CO3 (200 ml×3), 200 ml of water and 200 ml saturated NaCl, dried over anhydrous MgSO4, and filtered. The solvent was evaporated to give a straw yellow solid. The solid was recrystallized with a mixed solvent of ethyl acetate and petroleum ether (1:4) to give a white needle crystal (32.9 g). MS (m/z): 181 [M+1]+.

1. customTo a 500 ml three-neck flask equipped with a mechanical stirrer and an inert gas tube
2. extractionthe resultant mixture was extracted with ethyl acetate (600 ml×2)
3. washThe organic phase was washed with saturated Na2CO3 (200 ml×3), 200 ml of water and 200 ml saturated NaCl
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. customThe solvent was evaporated
7. customto give a straw yellow solid
8. customThe solid was recrystallized with a mixed solvent of ethyl acetate and petroleum ether (1:4)

ORD record

ord-b66c0809e0d14e62bb48b0a0ce8f35a9

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952178B2