Water → HCID 22574217, compound

HRID 1994216Notes

Reaction equation

HRID 1994216 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 is 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 is 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 till neutral. After drying over Na2SO4, the mixture is evaporated to dryness. Yield: 22.91 g of yellow oil (82% of theory).

Workup

  1. additionis 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 till neutral
  10. dry with materialAfter drying over Na2SO4
  11. customthe mixture is evaporated to dryness

Sources & evidence

ORD record
ord-595db1163d404f05bfb15223d3fa8688
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

Loading…