Hydroxyamine hydrochloride → HCID 86707701, compound

HRID 1408928Notes

Reaction equation

HRID 1408928 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[OH:9][C:10]1([CH3:18])[CH2:14][CH2:13][C:12](=O)[C:11]1([CH3:17])[CH3:16]>C(O)C.O>[OH:9][C:10]1([CH3:18])[CH2:14][CH2:13][C:12](=[N:7][OH:8])[C:11]1([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 68292267HCID 68292267, compound

Product 1

HCID 86707701HCID 86707701, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium acetate (7.57 g, 92 mmol) and hydroxylamine hydrochloride (6.01 g, 87 mmol) were added to a solution of 3-hydroxy-2,2,3-trimethylcyclopentanone (8.20 g, 57.7 mmol, from Step 1) in ethanol (80 mL) and water (16 mL). The resultant mixture was heated to 80° C. for 15 h, then cooled to room temperature. After removal of ethanol in vacuo, the aqueous residue was diluted with water (20 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated to give crude 3-hydroxy-2,2,3-trimethylcyclopentanone oxime (9.05 g). 1H NMR (400 MHz, methanol-d4) δ ppm 2.29-2.80 (2 H, m), 1.63-1.94 (2 H, m), 1.22 (3 H, s), 1.08 (3 H, s), 0.99 (3 H, s).

Workup

  1. customAfter removal of ethanol in vacuo
  2. additionthe aqueous residue was diluted with water (20 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45253087ebcb4c39ba69b0f533e54807
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

Loading…