Methyl iodide → Methyl 2,2'-dichlorobenzilate

HRID 1994211Notes

Reaction equation

HRID 1994211 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])([OH:8])[C:5]([OH:7])=[O:6].[O-][CH2:21]C.[Na+].[Na].CI>C(O)C.O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])([OH:8])[C:5]([O:7][CH3:21])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 3290602,2'-Dichlorobenzilic acidHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 22574193Methyl 2,2'-dichlorobenzilate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 10.0 g (0.034 mol) of 2,2′-dichlorobenzilic acid in 50 ml of ethanol was added dropwise to freshly prepared sodium ethoxide solution of 0.78 g (0.034 mol) of sodium and 100 ml of ethanol at 20° C. and stirred overnight. The solution was evaporated to dryness, the residue was dissolved in DMF and at 20° C. 9.57 g (0.0674 mol) of methyl iodide were added dropwise and the mixture was stirred for a further 72 hours. 300 ml of water were added dropwise to the resulting suspension while cooling with ice, it was extracted with diethyl ether, the organic phase was washed with water, dried over Na2SO4, and evaporated to dryness. Yield: 10.48 g (100% of theory).

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue was dissolved in DMF and at 20° C
  3. stirringthe mixture was stirred for a further 72 hours
  4. temperaturewhile cooling with ice, it
  5. extractionwas extracted with diethyl ether
  6. washthe organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5981b5f934ff40f2a05b76d0adb4853e
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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