Lithium Hydroxide → 4-(Dimethylcarbamoyl)benzoic acid

HRID 1808886Notes

Reaction equation

HRID 1808886 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>CO>[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11106558Methyl 4-(dimethylcarbamoyl)benzoate

Product 1

HCID 110954804-(Dimethylcarbamoyl)benzoic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a soln. of methyl 4-(dimethylcarbamoyl)benzoate (100 mg, 0.483 mmol, crude from above preparation) in MeOH (4 ml) was added LiOH (1 ml, 3.00 mmol). The mixture was stirred at r.t for 1.5 hrs. Evaporated to remove the solvent. The residue was dissolved in water (3 ml), neutralized w/6M HCl to PH=3, extracted w/EtOAc (3×). The combined organic layer was dried (Na2SO4) and evaporated to afford 4-(dimethylcarbamoyl)benzoic acid (64 mg, 0.315 mmol, 65.2% yield) as solid, which was used for the next reaction directly.

Workup

  1. customEvaporated
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved in water (3 ml)
  4. extractionextracted w/EtOAc (3×)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4a2e2d5c01b04df38d879fb7694bd8cd
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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