Reaction #5097

Reaction equation

2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one

hydroxylamine hydrochloride

pyridine

→

2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one oxime

Solvents

ethyl acetate

ethanol

ethanol

Conditions

Workup

1. 1
   Temperaturewas refluxed for 4 hours
2. 2
   Concentrationthe reaction mixture was concentrated to dryness under a reduced pressure
3. 3
   Otherthe residue thus obtained
4. 4
   Washwashed three times with 1 liter of water each time
5. 5
   Otherthe residue was dried again under a reduced pressure
6. 6
   OtherRecrystallized from ethyl acetate/n-hexane mixture

Procedure

An ethanol solution containing 120 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one, 45 of hydroxylamine hydrochloride and 200 ml of pyridine in 1,200 ml of ethanol was refluxed for 4 hours. After the reaction was completed, the reaction mixture was concentrated to dryness under a reduced pressure, then the residue thus obtained was dissolved in 2 liters of ethyl acetate and washed three times with 1 liter of water each time, and the residue was dried again under a reduced pressure. Recrystallized from ethyl acetate/n-hexane mixture to obtain 90 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one oxime. Light yellow flake-like crystals. Melting point: 146° C. (Decomposed).

Source