Diethyl Ether → 4-Hydroxyimino-6-phenyl-hexanoic acid

HRID 852892Notes

Reaction equation

HRID 852892 reaction equation
O=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Cl.[NH2:17][OH:18].C[O-].[Na+].CCOCC>CO>[OH:18][N:17]=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 6097734-Oxo-6-phenylhexanoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 600707174-Hydroxyimino-6-phenyl-hexanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ketone 99 (3.0 g, 13.6 mmol) and hydroxylamine hydrochloride (1.98 g, 27 mmol) were dissolved in methanol (20 mL) then sodium methoxide (2.9 g) was added. The solution was stirred and refluxed for 2 hr then cooled. Ether was added and the organic layer was washed twice with 2M HCl, brine and dried over MgSO4. Removal of solvent gave the oximes 100 (2.7 g 90%) as a mixture of E:Z isomers in the ratio 1.5:1.

Workup

  1. temperaturerefluxed for 2 hr
  2. temperaturethen cooled
  3. washthe organic layer was washed twice with 2M HCl, brine
  4. dry with materialdried over MgSO4
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-5353d4ad944d49e7bce5b3d97acdda7e
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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