Dimethyl Sulfate → 3-ethoxy-2-methoxybenzaldehyde
Reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12])[CH3:2].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[C:5]([O:12][CH3:13])=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of 3-ethoxysalicylaldehyde (1.00 g, 6.02 mmol) and potassium carbonate (3.33 g, 24.1 mmol) in N,N-dimethylformamide (10 mL) was added dimethyl sulfate (0.91 g, 7.22 mmol), and the mixture was stirred at 60° C. for 5 hours. The reaction mixture was diluted with ethyl acetate, filtered, and the filtrate was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (1.10 g, yield 99%) as an oily matter.
Workup
- filtrationfiltered
- washthe filtrate was washed with water
- concentrationconcentrated under reduced pressure
- customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3)
Sources & evidence
- ORD record
- ord-c2db3961a91c4e36a95bf12787835c79
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008525B2
Reaction notes
Loading…