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

HRID 1005294Notes

Reaction equation

HRID 1005294 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].OO.[OH2:20].C(O)(=[O:23])C>[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:23])(=[O:20])[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-methylthiochroman-7-carboxylic acid are initially introduced in 60 ml of acetic acid. A spatula tipful of sodium tungstate is added. 7.9 g (0.07 mol) is of 30% strength hydrogen peroxide solution are slowly added dropwise at 50° C. and the reaction mixture is subsequently stirred for 2 hours. It is then poured into water and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with bisulfite solution, then dried and concentrated.

Workup

  1. additionare slowly added dropwise at 50° C.
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe organic phase is washed with bisulfite solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-961c88133be2439b95f8b5023c1bc999
Source dataset
uspto-grants-2000_04
Patent number
US06054414

Reaction notes

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