Methyl iodide → Di-p-tolylhydroxyacetic acid methyl ester

HRID 1994214Notes

Reaction equation

HRID 1994214 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[O-][CH2:21]C.[Na+].[Na].CI>C(O)C.O>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:19][CH:18]=2)([OH:10])[C:7]([O:9][CH3:21])=[O:8])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 229097Hydroxy[bis(4-methylphenyl)]acetic acidHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 22574226Di-p-tolylhydroxyacetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

At 20° C., 12.43 g (0.048 mol) of 4,4′-dimethylbenzilic acid in 50 ml ethanol is added dropwise to freshly prepared sodium ethoxide solution containing 1.1 g (0.045 mol) of sodium and 100 ml of ethanol and the mixture is stirred for 30 minutes. The solution is evaporated to dryness, the residue dissolved in 50 ml of DMF, 9.08 g (0.064 mol) of methyl iodide is added dropwise at 20° C., and stirring is continued for a further 24 hours. 300 ml of water are added dropwise to the resulting suspension while cooling with ice, the mixture is extracted with diethylether; the organic phase is washed with water, dried over Na2SO4, and evaporated to dryness. Yield: 8.6 g (99% of theory); melting point: 83° C.-84° C.

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue dissolved in 50 ml of DMF
  3. stirringstirring
  4. waitis continued for a further 24 hours
  5. temperaturewhile cooling with ice
  6. extractionthe mixture is extracted with diethylether
  7. washthe organic phase is washed with water
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-2a677abf392f4e1da1bef3bb796b8eaf
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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