Methyl iodide → HCID 12395564, compound

HRID 1679712Notes

Reaction equation

HRID 1679712 reaction equation
[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([Cl:16])[C:8]([Cl:15])=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:17])([CH3:3])[CH3:2].[H-].[Na+].[CH3:20]I>COCCOC>[CH3:20][C:4]1([CH:1]([CH3:3])[CH3:2])[CH2:12][C:11]2[C:6](=[C:7]([Cl:16])[C:8]([Cl:15])=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12395556HCID 12395556, compound

Product 1

HCID 12395564HCID 12395564, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
30 °C

Procedure

A stirred suspension of 2-isopropyl-5-methoxy-6,7-dichloro-1-indanone (7.3 g., 0.025 mole) and sodium hydride (810 mg., 0.028 mole) in anhydrous 1,2-dimethoxyethane (250 ml.) is heated in an inert atmosphere at 80°-85° C. for 1 hour, cooled to 30° C. and treated with methyl iodide (6 ml.). The reaction mixture is heated to 80° C., then the solvent is distilled at reduced pressure and the residue poured into ice water. The 2-methyl-2-isopropyl-5-methoxy-6,7-dichloro-1-indanone which separates (7.0 g.) melts at 143° C. after recrystallization from ethanol-water.

Workup

  1. temperatureis heated in an inert atmosphere at 80°-85° C. for 1 hour
  2. temperatureThe reaction mixture is heated to 80° C.
  3. distillationthe solvent is distilled at reduced pressure
  4. additionthe residue poured into ice water
  5. customafter recrystallization from ethanol-water

Sources & evidence

ORD record
ord-700b816d3fa947668c2ce7ae8e2c77f3
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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