Acetophenone → Acetophenonoxime

Acetophenone (5.0 mL, 43 mmol) was dissolved in methanol (50 mL). Hydroxylamine hydrochloride (6.1 g, 88 mmol) was added to the mixture followed by 10N sodium hydroxide (10 mL, 100 mmol). Reaction was stirred at room temperature for 20 minutes. 10N Sodium hydroxide (5 mL, 50 mmol) was added to the mixture. Reaction was heated at reflux for 1 hour. Mixture was cooled to room temperature and stirred for 4 hours. Reaction mixture was concentrated in vacuo. Residue was treated with water. Mixture was extracted 2× diethyl ether. Combined extracts were washed 1× water, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated. Title compound was obtained as white solid in 76% yield. MS m/e (M+H)+=136.0.

1. customReaction
2. customReaction
3. temperaturewas heated
4. temperatureat reflux for 1 hour
5. temperatureMixture was cooled to room temperature
6. stirringstirred for 4 hours
7. customReaction mixture
8. concentrationwas concentrated in vacuo
9. additionResidue was treated with water
10. extractionMixture was extracted 2× diethyl ether
11. washCombined extracts were washed 1× water, 1× brine
12. dry with materialOrganic layer was dried (magnesium sulfate)
13. filtrationfiltered
14. concentrationconcentrated

ORD-Eintrag

ord-e6c8081b6d984884b658c97522b2f314

Quelldatensatz

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07384931B2