Reaktion #85444

Reaktionsgleichung

compound 563-E

3-Isopropyl-benzo[b]thiophene-2-carboxaldehyde

potassium permanganate

→

compound 563-F

Ausbeute 72.6%

3-Isopropyl-benzo[b]thiophene-2-carboxylic acid

Ausbeute 72.6%

Lösungsmittel

H2O

acetone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added in portions
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.ADDITIONA solution of aqueous Na2SO3 (1M, 50 mL) was added
4. 4
   workup.ADDITIONTwo additional portions of Na2SO3 (1M, 20 mL) were added
5. 5
   Sonstigeresulted in the disappearance of the dark brown color
6. 6
   Filtrationfiltered
7. 7
   Waschenwashed with H2O
8. 8
   Sonstigedried under vacuo

Vorschrift

A solution of compound 563-E (1.95 g, 9.5 mmol) in acetone (30 mL) was refluxed for 30 min. A mixture of potassium permanganate (3.02 g, 19.1 mmol) in water (10 mL) was added in portions, and the resultant mixture was refluxed for an additional 30 min. The mixture was cooled to ambient temperature and concentrated in vacuo. A solution of aqueous Na2SO3 (1M, 50 mL) was added followed by sulfuric acid (1M, 50 mL). Two additional portions of Na2SO3 (1M, 20 mL) were added followed by sulfuric acid (1M, 20 mL), which resulted in the disappearance of the dark brown color. The resultant suspension was diluted with H2O, filtered, washed with H2O and dried under vacuo to afford 1.52 g of compound 563-F as a yellow solid. MS: m/z 221.1 (MH+).

Quelle