Potassium Hydroxide → 2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid

HRID 842723Notes

Reaction equation

HRID 842723 reaction equation
[CH2:1]1[CH2:12][O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[O:2]1.[Mn]([O-])(=O)(=O)=[O:14].[K+].[OH-].[K+]>O>[CH2:1]1[CH2:12][O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]([OH:14])=[O:6])[O:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

Product 1

HCID 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acidYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a 500 ml round bottom flask fitted with a 250 ml addition funnel and a magnetic stir bar were placed 2,3-ethylenedioxybenzaldehyde (4.07 g, 24.7 mmol) and 100 ml of water. The mixture was heated to 80° and potassium permanganate (7.84 g, 49.6 mmol) in 150 ml of water was added dropwise via the addition funnel over 20 minutes. After the addition was complete the mixture was allowed to stir at 80° for 1.5 hours. The mixture was made basic with a 10% potassium hydroxide solution and the solids filtered. The filter cake was washed with hot water. The filtrate was extracted with ether, made acidic, then extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered, and concentrated to give 2.96 g of subtitled product (66%) which was used directly in the next step.

Workup

  1. customInto a 500 ml round bottom flask fitted with a 250 ml addition funnel and a magnetic stir bar
  2. temperatureThe mixture was heated to 80°
  3. additionAfter the addition
  4. filtrationthe solids filtered
  5. washThe filter cake was washed with hot water
  6. extractionThe filtrate was extracted with ether
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organics were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d48e2b60829e4100bf1c21f619b8460a
Source dataset
uspto-grants-2002_04
Patent number
US06376505B1

Reaction notes

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