Hydrochloric Acid → HCID 86707700, compound

HRID 1408926Notes

Reaction equation

HRID 1408926 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[OH:9][CH:10]1[CH2:14][CH2:13][C:12](=O)[C:11]1([CH3:17])[CH3:16].Cl>C(O)C.O>[OH:9][CH:10]1[CH2:14][CH2:13][C:12](=[N:7][OH:8])[C:11]1([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22505716HCID 22505716, compound

Product 1

HCID 86707700HCID 86707700, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium acetate (3.58 g, 43.7 mmol) and hydroxylamine hydrochloride (2.85 g, 41.0 mmol) were added to a solution of 3-hydroxy-2,2-dimethylcyclopentanone (3.50 g, 27.3 mmol, from Step 1) in ethanol (50 mL) and water (10 mL). The resultant mixture was heated to 80° C. for 15 h, cooled to room temperature and acidified to pH 2-3 with 1 N hydrochloric acid. After removal of ethanol in vacuo, the aqueous residue was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated, to give 3-hydroxy-2,2-dimethylcyclopentanone oxime (3.60 g, 92% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 3.76 (1 H, t, J=6.16 Hz), 2.51-2.80 (1 H, m), 2.32-2.53 (1 H, m), 1.91-2.16 (1 H, m), 1.58-1.81 (1 H, m), 0.92-1.13 (6 H, m).

Workup

  1. customAfter removal of ethanol in vacuo
  2. extractionthe aqueous residue was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1d643df763e4fc5a7e1a8212e261a0a
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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