Sodium Hydroxide → 5-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid

HRID 260719Notes

Reaction equation

HRID 260719 reaction equation
[CH3:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].[OH-].[Na+].S([O-])([O-])=[O:17].[Na+].[Na+]>O1CCCC1.[C].[Pd]>[CH3:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:12]([OH:17])=[O:13]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 157675575-Methyl-2,3-dihydrobenzo[B][1,4]dioxine-6-carbaldehyde

Product 1

HCID 107029595-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acidYield 61%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was dissolved 0.8 g of 5-methyl-1,4-benzodioxan-6-carbaldehyde, then 27 ml of a 1% sodium hydroxide aqueous solution was added dropwise to the solution and further 0.5 g of a 10% palladium-carbon was added thereto, and the mixture was refluxed under heating for 1.5 days. The mixture was cooled to room temperature, 10 ml of a 10% sodium sulfite aqueous solution was added thereto and after stirring for 30 minutes, the mixture was filtered and the tetrahydrofuran was removed under reduced pressure. The residue was adjusted to pH 3 with a 5% hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was washed successively with water and saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 0.53 g of the titled 5-methyl-1,4-benzodioxan-6-carboxylic acid (yield: 61%).

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 1.5 days
  4. filtrationthe mixture was filtered
  5. customthe tetrahydrofuran was removed under reduced pressure
  6. extractionextracted with diethyl ether
  7. washThe diethyl ether layer was washed successively with water and saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-622b5c3acffe4cab80a7ba51011c7730
Source dataset
uspto-grants-1996_06
Patent number
US05530021

Reaction notes

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