Potassium Iodide → HCID 3363782, compound
Reaction equation
[CH2:1](Br)[CH2:2][CH3:3].[OH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:7]=1[CH:8]=[O:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CN(C)C=O>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:6]([O:5][CH2:1][CH2:2][CH3:3])[C:7]=1[CH:8]=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Propyl bromide (1 ml) was added to a mixture of 2-hydroxy-6-methoxybenzaldehyde (0.45 g), potassium carbonate (0.83 g) and a small amount of potassium iodide in a mixed solvent of N,N-dimethylformamide (10 ml) and acetone (5 ml). After being stirred for 5 hours at 100° C., the mixture was poured into ice-water (20 ml) and extracted with ethyl acetate. The extract was washed with brine (10 ml), dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless oil of 2-methoxy-6-propoxybenzaldehyde (0.3 g).
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with brine (10 ml)
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1)
- additionThe fractions containing the objective compound
- customwere collected
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-57fd4b8752e44f51aa49ac4e030896fe
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06787543B2
Reaction notes
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