Methanol → methyl (4E)-4-hydroxyimino-4-phenylbutanoate

HRID 1836420Notes

Reaction equation

HRID 1836420 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+].CO>C(OCC)(=O)C.CCCCCC>[OH:17]/[N:16]=[C:1](/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)\[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoateYield 91%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of methyl 3-benzoylpropionate (15.0 9), hydroxylamine hydrochloride (6.50 g), sodium acetate (9.60 g) and methanol (150 ml) was heated under reflux for 8 hours. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with water, dried (over MgSO4) and concentrated. The residue was subjected to a silica gel column chromatography and, from an eluate with ethyl acetate-hexane (1:3, volume ratio), methyl (E)-4-hydroxyimino-4-phenylbutyrate (14.7 g; yield: 91%) was obtained as an oily product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate The ethyl acetate layer
  6. washwas washed with water
  7. dry with materialdried (over MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-23c16e1069f346f4bd6471bf2a6ff624
Source dataset
uspto-grants-2004_08
Patent number
US06777435B1

Reaction notes

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