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

HRID 1620630Notes

Reaction equation

HRID 1620630 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 (60 mL) was added 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, and dried over magnesium sulfate 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 magnesium sulfate

Sources & evidence

ORD record
ord-ecb204521782467496900e40b760d6d4
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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