Sodium Hydroxide → HCID 57686825, compound

HRID 251815Notes

Reaction equation

HRID 251815 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:18]([O:20]C)=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14]>CCO>[CH3:16][O:15][C:13]([C:12]1[CH:11]=[C:10]([CH:9]=[C:8]([O:7][CH2:6][CH2:5][O:4][CH3:3])[CH:17]=1)[C:18]([OH:20])=[O:19])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57686823HCID 57686823, compound

Product 1

HCID 57686825HCID 57686825, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

NaOH (45 mmol) was added to the solution of dimethyl 5-(2-methoxyethoxy)isophthalate (30 mmol) in 50 ml EtOH and stirred for 4 h at 40° C. Excess of solvent was removed in vacuo and the residue was treated with 1N HCl (aqueous) and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated to afford 3-(methoxycarbonyl)-5-(2-methoxyethoxy)benzoic acid (87.3%).

Workup

  1. customExcess of solvent was removed in vacuo
  2. additionthe residue was treated with 1N HCl (aqueous)
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ee770ee0c514f969be34953de84fe2a
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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