Water → HCID 13391258, compound

HRID 2412404Notes

Reaction equation

HRID 2412404 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=[O:14].[OH2:16]>N1C=CC=CC=1>[S:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:4]([CH:1]([OH:3])[C:2]([OH:14])=[O:16])=[CH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 143163-AcetylbenzothiopheneHCID 24007Selenium Dioxide

Product 1

HCID 13391258HCID 13391258, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Eleven grams of the 3-acetylbenzothiophene from above was dissolved in 80 ml of pyridine and warmed to 60° C. To the reaction mixture were added portionwise 9.92 g of selenium dioxide. The reaction mixture was warmed to 120° C. and then cooled to 90° C. and stirred at that temperature for forty-five minutes. The mixture was next added to 80 ml of water, and the pyridine solvent was then removed by evaporation. The aqueous mixture was acidified to pH 2.0 with phosphoric acid, and the product was extracted into diethyl ether. Removal of the solvent by evaporation and crystallization of the product from benzene gave 3.85 g of 3-benzothienylglycolic acid. m.p. 89°-91° C.

Workup

  1. temperatureThe reaction mixture was warmed to 120° C.
  2. temperaturecooled to 90° C.
  3. customthe pyridine solvent was then removed by evaporation
  4. extractionthe product was extracted into diethyl ether
  5. customRemoval of the solvent
  6. customby evaporation and crystallization of the product from benzene

Sources & evidence

ORD record
ord-95f3e735c83843a09d4dd6ffbffe92f0
Source dataset
uspto-grants-1985_01
Patent number
US04492693

Reaction notes

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