Sodium Hydroxide → 7-Hydroxy-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

HRID 37161Notes

Reaction equation

HRID 37161 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][CH:13]([C:16]([O:18]CC)=[O:17])[O:12][C:11]=2[CH:21]=1)(=O)C>CO>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[O:12][C:11]=2[CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10858395Ethyl 7-acetoxy-2,3-dihydro-1,4-benzodioxin-2-carboxylate

Product 1

HCID 108995517-Hydroxy-2,3-dihydro-1,4-benzodioxine-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, slowly add 75 mmol of a 10% aqueous sodium hydroxide solution to a solution of 2 g (7.5 mmol) of ethyl 7-acetoxy-2,3-dihydro-1,4-benzodioxin-2-carboxylate in 20 cm3 of methanol. Stir at room temperature for 6 hours and then, after concentrating under reduced pressure, acidify the mixture with a 2N hydrochloric acid solution. Extract with diethyl ether the acid which precipitates, then, after drying and concentration to dryness, wash the resulting acid with methylene chloride. 7-Hydroxy-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid is thereby obtained in a yield of 85%.

Workup

  1. concentrationafter concentrating under reduced pressure
  2. extractionExtract with diethyl ether the acid which
  3. customprecipitates
  4. customafter drying
  5. concentrationconcentration to dryness
  6. washwash the resulting acid with methylene chloride

Sources & evidence

ORD record
ord-a34cd75a3c294cadabed2fc1ac5336bf
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Reaction notes

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