Methyl iodide → 2,2-Dimethyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1287428Notes

Reaction equation

HRID 1287428 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

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 123955612-Methyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 123955652,2-Dimethyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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 one 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

  1. temperatureis heated in an inert atmosphere at 80°-85° C. for one hour
  2. temperatureis refluxed for 15 minutes
  3. distillationthe solvent is distilled at reduced pressure
  4. additionThe crude product is poured into water (500 ml.)
  5. extractionextracted into ether
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customAfter evaporation of the ether the product
  9. customis crystallized from methylcyclohexane affording 8.2 g

Sources & evidence

ORD record
ord-cca974b873e64963a0794910039a078e
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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