Methyl iodide → Methyl 2-(2,4-dichlorophenyl)propanoate

HRID 745273Notes

Reaction equation

HRID 745273 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].I[CH3:17]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:17])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2734106Methyl 2,4-dichlorobenzeneacetate

Product 1

HCID 23315465Methyl 2-(2,4-dichlorophenyl)propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 22 parts of methyl 2,4-dichlorobenzeneacetate and 135 parts of N,N-dimethylformamide are added 3.1 parts of sodium hydride dispersion 78% while nitrogen gas is introduced. The whole is stirred till foaming has ceased and cooled in an ice-bath. Then there are added dropwise 16 parts of iodomethane. Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto water and the product is extracted with 2,2'-oxybispropane. The extract is washed with water, dried, filtered and evaporated, yielding 20 parts (80%) of methyl 2,4-dichloro-α-methylbenzeneacetate as a residue.

Workup

  1. additionis introduced
  2. temperaturecooled in an ice-bath
  3. stirringUpon completion, stirring
  4. additionThe reaction mixture is poured onto water
  5. extractionthe product is extracted with 2,2'-oxybispropane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a873e3eb455047f9ae7d6977df926573
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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