Reaction #155314

Reaction equation

1-(3-Propoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone

Hydroxylamine hydrochloride

pyridine

→

1-(3-propoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone oxime

Yield 94.0%

Solvents

chloroform

methanol

Conditions

Workup

1. 1
   Temperaturewhile heating
2. 2
   Temperatureunder reflux
3. 3
   Concentrationconcentrated to dryness under reduced pressure
4. 4
   workup.ADDITION2N hydrochloric acid (30 ml) and water were added to the residue
5. 5
   Extractionfollowed by extraction
6. 6
   ConcentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
7. 7
   Otherthe residue was then purified
8. 8
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

1-(3-Propoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (8.88 g, 38.2 mmol) was dissolved in a mixed solvent of chloroform (20 ml) and methanol (80 ml). Hydroxylamine hydrochloride (4.05 g, 58.2 mmol) and pyridine (9.46 ml, 117 mmol) were added to the solution and stirred for 16 hours while heating under reflux. The reaction mixture was cooled to room temperature, and then concentrated to dryness under reduced pressure. 2N hydrochloric acid (30 ml) and water were added to the residue, followed by extraction using dichloromethane. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the residue was then purified using silica gel column chromatography (n-hexane: ethyl acetate=5:1). The purified product was concentrated to dryness under reduced pressure, giving a pale yellow powder of 1-(3-propoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone oxime (8.87 g, yield: 94%).

Source