Sodium Hydroxide → 3-Methoxy-5-(methoxycarbonyl)benzoic acid

HRID 1791343Notes

Reaction equation

HRID 1791343 reaction equation
[CH3:1][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+]>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4167302Dimethyl-5-methoxyisophthalate

Product 1

HCID 110201363-Methoxy-5-(methoxycarbonyl)benzoic acidYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of dimethyl-5-methoxy-isophthalate (6.4 g, 28.5 mmol) in methanol (143 mL) was treated with 1 N sodium hydroxide (25.6 mL, 25.6 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1 N HCl to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulfate. After removal of solvent in vacuo, 4.5 g (75%) of 5-methoxyisophthalic acid monomethyl ester was isolated as a white solid. 1H NMR (DMSO), δ(ppm): 8.17 (m, 1H), 7.60 (m, 2H), 3.80 (s, 3H), 3.76 (s, 3H).

Workup

  1. waitThe reaction was left
  2. concentrationAfter the solution was concentrated
  3. dissolutionthe residue was dissolved in water
  4. customtransferred to a separatory funnel
  5. washThe aqueous layer was washed with dichloromethane (3 times)
  6. extractionto extract the precipitate, which
  7. washwas then washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter removal of solvent in vacuo

Sources & evidence

ORD record
ord-7993330f56544394abc27c1cca50f87f
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

Loading…