Sodium Carbonate → 1,4-Benzodioxane-6-carboxylic Acid

HRID 858292Notes

Reaction equation

HRID 858292 reaction equation
Cl[O-].[Ca+2].Cl[O-].[OH-].[Na+].[C:8](=[O:11])([O-])[O-:9].[Na+].[Na+].[O:14]1[C:19]2[CH:20]=[CH:21][C:22](C(C)=O)=[CH:23][C:18]=2[O:17][CH2:16][CH2:15]1>O>[CH2:15]1[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:8]([OH:9])=[O:11])=[CH:20][C:19]=2[O:14]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24504Calcium hypochloriteHCID 761431,4-Benzodioxan-6-yl methyl ketone

Product 1

HCID 27588331,4-Benzodioxane-6-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 80.1 g of calcium hypochlorite in 360 ml of water and a suspension of 6.72 g of sodium hydroxide and 56.4 g of sodium carbonate in 170 ml of water are combined and heated to 50° C. with stirring. The precipitate is removed by filtration and the solution obtained is combined with 25.0 g of 1,4-benzodioxan-6-yl-methylketone. The mixture is stirred for 15 h at 60° C., and after cooling to ambient temperature extracted with ethyl acetate. The aqueous phase is adjusted to a pH of 3 by the addition of concentrated hydrochloric acid while cooling with ice. The product precipitated is suction filtered, washed with water and dried at 90° C.

Workup

  1. customThe precipitate is removed by filtration
  2. customthe solution obtained
  3. stirringThe mixture is stirred for 15 h at 60° C.
  4. temperatureafter cooling to ambient temperature
  5. extractionextracted with ethyl acetate
  6. additionThe aqueous phase is adjusted to a pH of 3 by the addition of concentrated hydrochloric acid
  7. temperaturewhile cooling with ice
  8. customThe product precipitated
  9. filtrationfiltered
  10. washwashed with water
  11. customdried at 90° C.

Sources & evidence

ORD record
ord-061c749223d84ac594329cf67cf1abf4
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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