Hydroxyamine hydrochloride → ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetate

HRID 2299705Notes

Reaction equation

HRID 2299705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[OH:18]/[N:17]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

Product 1

HCID 11770071ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetateYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-methoxyphenylglyoxylate (15.0 g), hydroxylamine hydrochloride (6.00 g), sodium acetate (8.86 g) and ethanol (150 ml) was heated under reflux for 12 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel and ethyl Z-2-hydroxyimino-2-(4-methoxyphenyl)acetate (8.99 g, yield 56%) was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless crystals. m.p. 81-82° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7baf4b63e2d94cefb91cee8f09b44e56
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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