Water → 2-[4-(2-Hydroxyiminocyclohexan-1-ylmethyl)phenyl]propionic Acid

HRID 971868Notes

Reaction equation

HRID 971868 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.Cl.[NH2:21][OH:22].O.O.O.C([O-])(=O)C.[Na+].O>C(O)C>[OH:22][N:21]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 133914932-(4-((2-Oxocyclohexyl)methyl)phenyl)propanoic acidHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 737697732-[4-(2-Hydroxyiminocyclohexan-1-ylmethyl)phenyl]propionic AcidYield 107.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.3 g of 2-[4-(2-oxocyclohexan-1-ylmethyl)phenyl]propionic acid, 0.33 g of hydroxylamine hydrochloride and 1.6 g of sodium acetate trihydrate in 85% ethanol was heated with stirring at 70°-75° C. for 2 hours, and the mixture was poured into 100 ml of water and extracted with ether. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 1.4 g of the desired compound, which by recrystallization from a mixture of ethyl acetate and n-hexane afforded colorless prisms, m.p. 143°-150.5° C.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-9ea146a4363d467f8afc88b4fb100801
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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