Potassium Carbonate → 6-Methoxy-1-tetralone oxime

HRID 1953634Notes

Reaction equation

HRID 1953634 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:21][OH:22]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[N:21][OH:22])[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 141126-Methoxy-alpha-tetraloneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 52161626-Methoxy-1-tetralone oximeYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 6-methoxy-1-tetralone (40 g, 227 mmol), potassium carbonate (64 g, 462 mmol) and hydroxylamine.hydrochloride (63.2 g, 909 mmol) in methanol (500 mL) and water (56 mL) was refluxed for 2.5 hours. The potassium carbonate was filtered off, poured into ice (300 g) and water was added to total 1.5 L. The precipitate was collected to give 34.79 g (80%) of crude product, which recrystallized in methanol to give 20.4 g (47%) of a white solid.

Workup

  1. filtrationThe potassium carbonate was filtered off
  2. additionpoured into ice (300 g) and water
  3. additionwas added to total 1.5 L
  4. customThe precipitate was collected
  5. customto give 34.79 g (80%) of crude product, which
  6. customrecrystallized in methanol

Sources & evidence

ORD record
ord-f51808174040431eaed8504709bdb0ad
Source dataset
uspto-grants-2000_09
Patent number
US06117910

Reaction notes

Loading…