Water → HCID 22574217, compound

HRID 2099345Notes

Reaction equation

HRID 2099345 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)([OH:10])[C:7]([OH:9])=[O:8].[CH3:21]I.O>C(O)C.C(OCC)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)([OH:10])[C:7]([O:9][CH3:21])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 5360545SodiumHCID 22574206HCID 22574206, compound

Product 1

HCID 22574217HCID 22574217, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

From 100 mL of ethanol and 1.97 g (0.0855 mol) of sodium, a sodium ethoxide solution is prepared to which 26.6 g (0.0855 mol) of 3,3′-dichlorobenzilic acid in 50 mL of ethanol are added dropwise. The mixture is then stirred for 4 hours at ambient temperature. After the solvent has been distilled off, the residue is dissolved in 150 mL DMF and 24.27 g (0.171 mol) of methyl iodide are added dropwise, then stirred for another 24 hours. While cooling with ice, 300 mL of water and 200 mL of diethylether are added dropwise, the phases are separated, the aqueous phase is extracted with diethylether, then the organic phases are washed with Na2CO3 solution and shaken with water until neutral. After drying over Na2SO4, the mixture is evaporated to dryness. Yield: 22.91 g of yellow oil (82% of theory).

Workup

  1. additionare added dropwise
  2. distillationAfter the solvent has been distilled off
  3. dissolutionthe residue is dissolved in 150 mL DMF
  4. stirringstirred for another 24 hours
  5. additionare added dropwise
  6. customthe phases are separated
  7. extractionthe aqueous phase is extracted with diethylether
  8. washthe organic phases are washed with Na2CO3 solution
  9. stirringshaken with water until neutral
  10. dry with materialAfter drying over Na2SO4
  11. customthe mixture is evaporated to dryness

Sources & evidence

ORD record
ord-a2e5361e62614074ba9e5630f46c8dc9
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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