Hydrochloric Acid → 5-[2-Hydroxy-3-(methylsulfanyl)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 893988Notes

Reaction equation

HRID 893988 reaction equation
[OH:1][CH:2]([CH2:21][S:22][CH3:23])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:20])[CH:8]=[C:9]([C:15]([O:17]CC)=[O:16])[O:10]2.[OH-].[Na+].Cl>CC(C)=O>[OH:1][CH:2]([CH2:21][S:22][CH3:23])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:20])[CH:8]=[C:9]([C:15]([OH:17])=[O:16])[O:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12888660Ethyl 5-(2-hydroxy-3-methylthiopropoxy)chromone-2-carboxylate

Product 1

HCID 30860675-[2-Hydroxy-3-(methylsulfanyl)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acidYield 89.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3.4 g of ethyl 5-(2-hydroxy-3-methylthiopropoxy)chromone-2-carboxylate in 20 ml of acetone there is added 11 ml of N sodium hydroxide and the mixture is heated at 50° C. for 10 minutes. After evaporating the solvent under reduced pressure, 30 ml of water are added, the resulting mixture is extracted with diethyl ether, filtered on charcoal and the limpid solution thus obtained is acidified with hydrochloric acid. The product which precipitates is filtered, washed with water and dried. Thus, 2.8 g of 5-(2-hydroxy-3-methylthiopropoxy)chromone-2-carboxylic acid is obtained as dihydrate (CM 57202); m.p. 76°-79° C.

Workup

  1. customAfter evaporating the solvent under reduced pressure, 30 ml of water
  2. additionare added
  3. extractionthe resulting mixture is extracted with diethyl ether
  4. filtrationfiltered on charcoal
  5. customthe limpid solution thus obtained
  6. customThe product which precipitates
  7. filtrationis filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-df7d36e322714315860f889fb0aac1f0
Source dataset
uspto-grants-1981_08
Patent number
US04282247

Reaction notes

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