Acetic Acid → 8-Methyl-1-oxothiochroman-4-one-7-carboxylic acid

HRID 1596765Notes

Reaction equation

HRID 1596765 reaction equation
[CH3:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][C:7]2=[O:12].C(O)(=[O:18])C.OO>[O-][W]([O-])(=O)=O.[Na+].[Na+].O>[CH3:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[S:10](=[O:18])[CH2:9][CH2:8][C:7]2=[O:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 153352288-Methylthiochroman-4-one-7-carboxylic acid

Product 1

HCID 153352408-Methyl-1-oxothiochroman-4-one-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 962WaterSolvent

Procedure

7.0 g (31.5 mmol) of 8-methylthiochroman-4-one-7-carboxylic acid together with one spatula-tip full of sodium tungstate are introduced into 70 ml of acetic acid. 3.6 g (31.5 mmol) of a 30% strength hydrogen peroxide solution are added dropwise at 50° C. Stirring is continued for 3 hours. The reaction solution is then stirred into water. The product is extracted using ethyl acetate. The organic phase is dried and the solvent is removed. The product is purified by chromatography.

Workup

  1. extractionThe product is extracted
  2. customThe organic phase is dried
  3. customthe solvent is removed
  4. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-83a9fd7a24db47d19ee919f51254fbd2
Source dataset
uspto-grants-2001_09
Patent number
US06291682B1

Reaction notes

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