Hydrochloric Acid → HCID 14820155, compound
Reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:13]([C:8]1[C:9]([OH:11])=[CH:10][C:3]([OH:2])=[C:4]([CH:7]=1)[CH:5]=[O:6])(=[O:15])[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 49.8 g of 2,4-dimethoxybenzaldehyde, 23.6 ml of acetyl chloride, and 1000 ml of methylene chloride cooled to approximately 0° C. were added 119.7 g of aluminum chloride with stirring under a nitrogen atmosphere. The reaction was allowed to warm to room temperature while stirring overnight. The mixture was added to a slurry of ice and concentrated hydrochloric acid. The organic layer was separated and washed with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The 15 residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-40% ethyl acetate in hexane gradient. The appropriate fractions were pooled and concentrated to provide 5.85 g of the desired title intermediate, m.p. =142°-143° C.
Workup
- temperatureto warm to room temperature
- stirringwhile stirring overnight
- customThe organic layer was separated
- washwashed with a saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe 15 residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-40% ethyl acetate in hexane gradient
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c12f3e8b471b4011bdeea4ecd639a713
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05098613
Reaction notes
Loading…