Methyl iodide → 2,2-Dimethyl-5-methoxy-6,7-dichloro-1-indanone
Reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15].[H-].[Na+].[CH3:18]I>COCCOC>[CH3:1][C:2]1([CH3:18])[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
A stirred suspension of 2-methyl-5-methoxy-6,7-dichloro-1-indanone (12.2 g., 0.05 mole) and sodium hydride (1.43 g., 0.06 mole) in anhydrous 1,2-dimethoxyethane (500 ml.) is heated in an inert atmosphere at 80°-85° C. for 1 hour, cooled to 30° C. and treated with methyl iodide (8 ml.). The reaction mixture is refluxed for 15 minutes, then the solvent is distilled at reduced pressure. The crude product is poured into water (500 ml.), extracted into ether, washed with water and dried over magnesium sulfate. After evaporation of the ether the product is crystallized from methylcyclohexane affording 8.2 g. of 2,2-dimethyl-5-methoxy-6,7-dichloro-1-indanone which melts at 142° C.
Workup
- temperatureis heated in an inert atmosphere at 80°-85° C. for 1 hour
- temperatureThe reaction mixture is refluxed for 15 minutes
- distillationthe solvent is distilled at reduced pressure
- additionThe crude product is poured into water (500 ml.)
- extractionextracted into ether
- washwashed with water
- dry with materialdried over magnesium sulfate
- customAfter evaporation of the ether the product
- customis crystallized from methylcyclohexane affording 8.2 g
Sources & evidence
- ORD record
- ord-2fc18d7ed3d24f8ab8be433b7baf09d7
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04012524
Reaction notes
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