Hydroxyamine hydrochloride → Methyl α-(hydroxyimino)-4-(1-methylethyl)benzeneacetate

HRID 1003969Notes

Reaction equation

HRID 1003969 reaction equation
Cl.[NH2:2][OH:3].O=[C:5]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]>CO>[OH:3][N:2]=[C:5]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18793911HCID 18793911, compound

Product 1

HCID 73856943Methyl α-(hydroxyimino)-4-(1-methylethyl)benzeneacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (0.87 g) was added to a stirred solution of the previously obtained mixture of methyl 2-oxo-2-(4-isopropyl-phenyl)acetate and methyl 4-isopropylphenyl acetate (1.29 g) in methanol (20 ml). When the solid had dissolved the mixture was left overnight. The solvent was evaporated and the residue partitioned between ethyl acetate and water, the organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The product (307 mg) was obtained by column chromatography of the residue using gradient elution (Kieselgel 3:1 to 1:1 hexane:ethyl acetate). νmax (CHCl3)/cm-1 3568, 3295 and 1738. δH (250 MHz, CDCl3), 1.28 (6H, d, J 6.87), 2.95 (1H, heptet, J 6.92), 3.88 (3H, s), 7.32 (2H, dd, J 1.81 and 6.47), 7.47 (2H, dd, J 1.83 and 6.65), 9.59 (1H, s).

Workup

  1. dissolutionWhen the solid had dissolved the mixture
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-e89874c31ead44ebb9bf24e795d15ea6
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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