Hydrochloric Acid → 4-(4-Methoxy-3-methylphenyl)-4-oxobutanoic acid
Reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.ClC(Cl)C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26].Cl>O.ClCCl>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][C:23]([C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[CH:24][C:19]=1[CH3:18]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of succinic anhydride (12.0 g, 122.0 mmol) and 50 mL of 1,1,2,2,-tetrachloroethane at room temperature was added AlCl3 (21.5 g, 161.2 mmol) and 2-methylanisole (Compound 1, 10 mL, 81.0 mmol). The resulting solution was stirred for 4 h at room temperature, then poured into a solution of concentrated HCl (20 mL) in water (50 mL) and ice. Dichloromethane was added, and the bottom layer was separated. The solvents were removed under reduced pressure, and the residue was dissolved in a boiling solution of sodium carbonate (30 g Na2CO3 in 160 mL H2O) for 10 min, and filtered. The filtrate was acidified with concentrated HCl to pH=0-1, and crystallized in a salt ice bath. The solid product was filtered and washed with cold water, and dried in the air to give 13.7 g (76%) of the title compound as an off-white solid.
Workup
- customthe bottom layer was separated
- customThe solvents were removed under reduced pressure
- dissolutionthe residue was dissolved in a boiling solution of sodium carbonate (30 g Na2CO3 in 160 mL H2O) for 10 min
- filtrationfiltered
- customcrystallized in a salt ice bath
- filtrationThe solid product was filtered
- washwashed with cold water
- customdried in the air
Sources & evidence
- ORD record
- ord-a5caa0ea45314c118975a5861ab9790c
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613917B1
Reaction notes
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