Lithium Hydroxide → 2,3-Dihydro-8-methoxy-1,4-benzodioxin-6-carboxylic acid

HRID 323401Notes

Reaction equation

HRID 323401 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]2[O:16][CH2:15][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:16][CH2:15][CH2:14][O:13][C:12]=12)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18464946Methyl 8-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

Product 1

HCID 49623162,3-Dihydro-8-methoxy-1,4-benzodioxin-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine methyl 3-methoxy-4,5-ethylenedioxybenzoate (0.46 g, 2.0 mmol) and tetrahydrofuran (15 mL). Add a 1 M aqueous solution of lithium hydroxide (2.5 mL, 2.5 mmol). Heat to reflux. After 15 hours, cool the reaction, concentrate in vacuo to remove most of the tetrahydrofuran. Cool in a ice bath and acidify with a 1 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. temperatureCool in a ice bath
  7. customto give a solid
  8. customCollect the solid
  9. filtrationby filtration
  10. customdry

Sources & evidence

ORD record
ord-c575280252474660a52bde61ea2b6db1
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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