Ethyl 4-oxocyclohexanecarboxylate → Cyclohexanecarboxylic acid, 4-(hydroxyimino)-, ethyl ester

HRID 1620558Notes

Reaction equation

HRID 1620558 reaction equation
Cl.[OH:2][NH2:3].C([O-])(=O)C.[Na+].O=[C:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1>O>[OH:2][N:3]=[C:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 11593553Cyclohexanecarboxylic acid, 4-(hydroxyimino)-, ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of hydroxyamine hydrochloride (15.3 g) and sodium acetate (24.1 g) in water (58.8 mL) was added dropwise ethyl 4-oxocyclohexanecarboxylate (25.0 g) over 20 min. The reaction mixture was stirred at room temperature overnight, and extracted with tert-butyl methyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (27.2 g).

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-81e6a70862f74c03ae8608fd9d89f527
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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