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

HRID 1005296Notes

Reaction equation

HRID 1005296 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 are initially introduced into 70 ml of acetic acid together with a spatula tipful of sodium tungstate. 3.6 g (31.5 mmol) of 30% strength hydrogen peroxide solution are added dropwise at 50° C. and the reaction solution is subsequently stirred for 3 hours. It is then stirred into water and the product is extracted with ethyl acetate. The organic phase is dried and the solvent is removed. The product is purified by chromatography.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. customThe organic phase is dried
  3. customthe solvent is removed
  4. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-e5d0bb2e75c041f1a97f30228d2dc922
Source dataset
uspto-grants-2000_04
Patent number
US06054414

Reaction notes

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