Acetic Acid → 8-Methyl-4-ethoxy-1,1-dioxothiochroman-7-carboxylic acid

HRID 1596763Notes

Reaction equation

HRID 1596763 reaction equation
[CH2:1]([O:3][CH:4]1[C:13]2[C:8](=[C:9]([CH3:17])[C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[S:7][CH2:6][CH2:5]1)[CH3:2].C(O)(=[O:20])C.OO.[OH2:24]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:17][C:9]1[C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=[C:13]2[C:8]=1[S:7](=[O:20])(=[O:24])[CH2:6][CH2:5][CH:4]2[O:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 153352344-Ethoxy-8-methylthiochroman-7-carboxylic acid

Product 1

HCID 153352378-Methyl-4-ethoxy-1,1-dioxothiochroman-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

8.4 g (0.033 mol) of 4-ethoxy-8-methylthiochromane-7-carboxylic acid are introduced into 60 ml of acetic acid. one spatula-tip full of sodium tungstate is added. 7.9 g (0.07 mol) of 30% strength hydrogen peroxide solution are slowly added dropwise at 50° C. Stirring is continued for 2 hours. The reaction batch is then poured into water and the aqueous phase is extracted using ethyl acetate. The organic phase is washed using bisulfite solution and then dried and concentrated.

Workup

  1. extractionthe aqueous phase is extracted
  2. washThe organic phase is washed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bab2d26c1af84f83b3fd84c1fa30d8f1
Source dataset
uspto-grants-2001_09
Patent number
US06291682B1

Reaction notes

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