Hydroxyamine hydrochloride → 2-Benzyl-3,4-dihydro-2H-naphthalen-1-one oxime

HRID 1369051Notes

Reaction equation

HRID 1369051 reaction equation
[CH2:1]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:25][OH:26]>C(O)C>[CH2:1]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[N:25][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5635332-Benzyl-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 861529872-Benzyl-3,4-dihydro-2H-naphthalen-1-one oximeYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-benzyl-1-tetralone (prepared according to Org. Prep. Proc. Inter., 2, 37 (1970)), (58.95 g, 0.250 mol) and 95% ethanol (500 mL) was added sodium acetate (45.1 g, 0.55 mol) and hydroxylamine hydrochloride (20.8 g, 0.30 mol). The reaction was heated to reflux overnight and then allowed to cool to room temperature and concentrated under vacuum. The residue was partitioned between water (300 mL) and ethryl acetate (500 mL), the organic layer was then sequentially washed with water (300 mL), and brine (500 mL). This was then dried over sodium sulfate and concentrated to give 61.1 g of an orange solid. Recrystalization from ethyl acetate/hexanes gave the title compound as a white solid, m.p. 123-124° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between water (300 mL) and ethryl acetate (500 mL)
  5. washthe organic layer was then sequentially washed with water (300 mL), and brine (500 mL)
  6. dry with materialThis was then dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40bd4a9a22534e0790812e76ae452565
Source dataset
uspto-grants-2003_06
Patent number
US06576632B1

Reaction notes

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