Methyl iodide → Benzilic acid

HRID 23377

Reaction equation

HRID 23377 reaction equation
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[O-]CC.[Na+].[Na].CI>C(O)C>[C:7]([OH:9])(=[O:8])[C:6]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([C:5]1[CH:18]=[CH:19][CH:2]=[CH:3][CH:4]=1)[OH:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 12068839Bis(4-fluorophenyl)(hydroxy)acetic acid

Product 1

HCID 6463Benzilic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.0 g (0.095 mol) of 4,4′-difluorobenzilic acid is added to freshly prepared sodium ethoxide solution containing 2.17 g (0.095 mol) of sodium and 200 ml of ethanol at 20° C. and stirred for 3 hours. The solution is evaporated to dryness, the residue is dissolved in DMF, 22.57 g (0.16 mol) of methyl iodide is added dropwise at 20° C., and the mixture is stirred for 24 hours. It is worked up and purified analogously to compound 12b. Yield: 21.06 g (80% of theory).

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in DMF
  3. stirringthe mixture is stirred for 24 hours
  4. custompurified analogously to compound 12b

Sources & evidence

ORD record
ord-aef3a9165c004a55b2384744041b864a
Source dataset
uspto-grants-2005_02
Patent number
US06852728B2

Linked notes

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