Sodium Methoxide → 3-(Ethoxymethyl)phthalic acid disodium salt

HRID 1751904Notes

Reaction equation

HRID 1751904 reaction equation
[CH2:1]([O:3][CH2:4][C:5]12O[CH:8]([CH:9]=[CH:10]1)[CH:7]1[C:12]([O:14][C:15](=[O:16])[CH:6]21)=[O:13])[CH3:2].C[O-:18].[Na+:19]>CO>[Na+:19].[Na+:19].[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O-:18])=[O:13])[C:6]=1[C:15]([O-:14])=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 894793071-Ethoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride2×

Product 1

HCID 894793053-(Ethoxymethyl)phthalic acid disodium saltYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 1, i.e., 1-ethoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (8 mmol) was, without purification, dissolved in methanol (10 ml). To this solution, solid sodium methoxide (0.86 g, 16 mmol) was added at 0° C. The resulting deep orange solution was stirred for 18 h at room temperature, after which the solvent was evaporated in vacuo. After drying for 1 h at 77° C. under reduced pressure, the solid was dissolved in water and heated under reflux for 5 h followed by treatment with charcoal (stirring for 30 min at reflux). Filtration and evaporation under reduced pressure yielded 3-(ethoxymethyl)phthalic acid disodium salt (37%).

Workup

  1. customafter which the solvent was evaporated in vacuo
  2. customAfter drying for 1 h at 77° C. under reduced pressure
  3. dissolutionthe solid was dissolved in water
  4. temperatureheated
  5. temperatureunder reflux for 5 h
  6. customfollowed by treatment with charcoal (stirring for 30 min at reflux)
  7. filtrationFiltration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-bc4484b08c564ce8ab54a9ad7c544c9e
Source dataset
uspto-grants-2015_10
Patent number
US09162960B2

Reaction notes

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