Methyl iodide → HCID 12395658, compound

HRID 1679741Notes

Reaction equation

HRID 1679741 reaction equation
[CH3:1][CH:2]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[C:5]([Cl:20])[C:6]([Cl:19])=[C:7]([O:17][CH3:18])[CH:8]=2)[C:3]1=[O:21].[CH3:22]I.C[O-].[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:22])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[C:5]([Cl:20])[C:6]([Cl:19])=[C:7]([O:17][CH3:18])[CH:8]=2)[C:3]1=[O:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 12395570HCID 12395570, compound

Product 1

HCID 12395658HCID 12395658, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-3-phenyl-5-methoxy-6,7-dichloro-1-indanone (9.63 g., 0.03 mole) and methyl iodide (18.7 ml., 0.3 mole) dissolved in dimethylformamide (100 ml.) at 25° C. under nitrogen are treated portionwise with sodium methoxide (4.2 g., 0.036 mole) over a 45 minute period. Sodium iodide is filtered off, and the yellow filtrate is added to water (500 ml.) to precipitate 6.57 g. of 2,2-dimethyl-3-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 146°-148° C. after crystallization from cyclohexane.

Workup

  1. filtrationSodium iodide is filtered off
  2. additionthe yellow filtrate is added to water (500 ml.)
  3. customto precipitate 6.57 g
  4. customof 2,2-dimethyl-3-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 146°-148° C. after crystallization from cyclohexane

Sources & evidence

ORD record
ord-29eff2e3ca66401b991b34af741e53f6
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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