Sodium Hydroxide → 5-Methoxybenzene-1,3-dicarboxylic acid

HRID 2216742Notes

Reaction equation

HRID 2216742 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:15][O:14][C:12]1[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=[C:4]([CH:13]=1)[C:3]([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4167302Dimethyl-5-methoxyisophthalate

Product 1

HCID 3274285-Methoxybenzene-1,3-dicarboxylic acidYield 114.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of dimethyl-5-methoxy-isophthalate (2.5 g, 11.1 mmol) in tetrahydrofuran/methanol (56 mL/20 mL) was treated with 2.0 N sodium hydroxide (12 mL, 25 mmol). The reaction was left stirring for 15 hours at room temperature. After the solution was concentrated, the solid was dissolved in water and acidified with 2.0 N hydrogen chloride. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 2.5 g (quantitative) of 5-methoxyisophthalic acid was isolated.

Workup

  1. waitThe reaction was left
  2. concentrationAfter the solution was concentrated
  3. dissolutionthe solid was dissolved in water
  4. extractionto extract the precipitate, which
  5. washwas then washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customAfter removal of solvent in vacuo

Sources & evidence

ORD record
ord-a980991c50084931bfcf76b8591ad4ae
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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