Lithium Hydroxide → 7-Methoxy-2H-1,3-benzodioxole-5-carboxylic acid

HRID 637132Notes

Reaction equation

HRID 637132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]2[O:15][CH2:14][O:13][C:12]=12)[C:6]([O:8]C)=[O:7].[OH-].[Li+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]2[O:15][CH2:14][O:13][C:12]=12)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoate

Product 1

HCID 6073097-Methoxy-2H-1,3-benzodioxole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine methyl 3-methoxy-4,5-methylenedioxybenzoate (0.84 g, 4.0 mmol) and tetrahydrofuran (25 mL). Add a 1 M aqueous solution of lithium hydroxide (8.0 mL, 8.0 mmol). Heat to reflux. After 4 hours, cool the reaction, concentrate in vacuo to remove most of the tetrahydrofuran. Extract with ethyl acetate. Cool in a ice bath and acidify the aqueous layer with a 6 M aqueous hydrochloric acid solution to give a solid. Collect the solid by filtration and dry to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customthe reaction
  4. concentrationconcentrate in vacuo
  5. customto remove most of the tetrahydrofuran
  6. extractionExtract with ethyl acetate
  7. temperatureCool in a ice bath
  8. customto give a solid
  9. customCollect the solid
  10. filtrationby filtration
  11. customdry

Sources & evidence

ORD record
ord-f3540da9804e46a186a63b859cd565ed
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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