Potassium Hydroxide → 1,4-Benzodioxane-6-carboxylic Acid

HRID 1271683Notes

Reaction equation

HRID 1271683 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Mn]([O-])(=O)(=O)=[O:14].[K+].[OH-].[K+]>O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:14])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516875Potassium Permanganate

Product 1

HCID 27588331,4-Benzodioxane-6-carboxylic AcidYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2,3-Dihydro-benzo[1,4]dioxine-6-carboxaldehyde (2.03 g, 12.4 mmol), was slurried in water (50 ml) at 80° C. Potassium permanganate (2.70 g, 17.1 mmol) as a solution in water (50 ml) was added over 1 hour. The mixture was then heated for a further 2 hours after which time the reaction mixture was basified with 10% aqueous potassium hydroxide. The resulting precipitate was removed by filtration and washed with water (2×50 ml). The combined filtrates were acidified with concentrated hydrochloric acid and the resulting solid isolated by filtration and dried under vacuum. This provided the desired compound as a white solid (1.50 g, 67%).

Workup

  1. temperatureThe mixture was then heated for a further 2 hours after which time the reaction mixture
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with water (2×50 ml)
  4. customthe resulting solid isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f494299f377c4c45bf9dc7b89da4e507
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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