2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid → Methyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate

HRID 581063Notes

Reaction equation

HRID 581063 reaction equation
[C:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:14](=O)([O-])O.[Na+].O.C(OCC)(=O)C>CN(C)C(=O)C>[CH3:14][O:2][C:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acidHCID 516892Sodium BicarbonateHCID 22728543Water ethylacetate

Product 1

HCID 15380892Methyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3.46 g (19.2 mmol) of the acid obtained in Step A are added to a mixture of 9.62 g (114.6 mmol) of sodium hydrogen carbonate and 3.57 ml (57.6 mmol) of iodomethanie in 40 ml of N,N-dimethylacetamide. After 24 hours' stirling under argon and protected from light, the solvent is removed by evaporation in vacuo. The residue obtained is then taken up in a 1/1 water/ethyl acetate mixture and the aqueous phase is subsequently extracted with ethyl acetate. After drying over magnesium sulphate and filtration, the solvent is removed by evaporation under reduced pressure. The title ester is obtained pure in the form of a white solid after chromatography over silica gel (eluant:AcOEt/PE:25/75).

Workup

  1. customthe solvent is removed by evaporation in vacuo
  2. customThe residue obtained
  3. extractionthe aqueous phase is subsequently extracted with ethyl acetate
  4. dry with materialAfter drying over magnesium sulphate and filtration
  5. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-22ffb7a00b9443d6a76cb9849b735bda
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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