3,4-dihydro-5,7-dimethylnaphthalen-1(2H)-one → 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one oxime

HRID 1375366Notes

Reaction equation

HRID 1375366 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=O.Cl.[NH2:15][OH:16].O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[N:15][OH:16]

Participants

5

Reactant 3

HCID 836193,4-dihydro-5,7-dimethylnaphthalen-1(2H)-oneHCID 443297Hydroxyamine hydrochlorideHCID 2735133Sodium Carbonate Monohydrate

Product 1

HCID 587943195,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one oximeYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5,7-Dimethyl-1-tetralone (5.0 g) in ethanol (100 mL) was treated with hydroxylamine hydrochloride (2.2 g) and sodium carbonate monohydrate (3.6 g). The reaction mixture was heated overnight at 80° C. with a condenser and behind a blast shield. Cooled to room temperature after seventeen hours, transferred to a 300 mL flask and concentrated. The residue was triturated in water and filtered to yield the title product as a beige solid (5.1 g).

Workup

  1. temperatureCooled to room temperature after seventeen hours
  2. customtransferred to a 300 mL flask
  3. concentrationconcentrated
  4. customThe residue was triturated in water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-674418b689894ef7b1abfc188346e873
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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