Triethylamine → (+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanone Oxime

HRID 585692Notes

Reaction equation

HRID 585692 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1.Cl.[NH2:17][OH:18].C(N(CC)CC)C>CN(C=O)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=[N:17][OH:18])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 12788196(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanone

Product 1

HCID 86586323(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanone OximeYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-3-(2,4-Dihydroxyphenyl)cyclohexanone (13 mg), hydroxylamine hydrochloride (0.0065 g), and triethylamine (16 μl) were heated at 80° C. in DMF (3 ml). After 3 hr, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 3:2 v/v) to furnish the title compound as a white solid (12 mg, 86%). δH (CD3OD) 1.4-2.0 (6H, overlapping m), 2.10 (0.5H, m), 2.20 (0.5H, m), 2.35 (0.5H, m), 2.46 (0.5H, m), 2.94 (1H, m), 6.22-6.26 (2H, overlapping m), 6.92-6.95 (1H, overlapping m); m/z (ES+) 222 (M+H)−.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 3:2 v/v)

Sources & evidence

ORD record
ord-3a780ee94282474aa801f14a9d5a893e
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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