Hydroxyamine hydrochloride → Ethyl 4-(1-(hydroxyimino)-2-methylpropyl)benzoate

HRID 1049087Notes

Reaction equation

HRID 1049087 reaction equation
[C:1]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)(=O)[CH:2]([CH3:4])[CH3:3].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>C(O)C>[OH:19][N:18]=[C:1]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 45116516Ethyl 4-isobutyrylbenzoate

Product 1

HCID 76779939Ethyl 4-(1-(hydroxyimino)-2-methylpropyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
36 °C

Procedure

A mixture of ethyl 4-isobutyrylbenzoate (0.56 g, 2.54 mmol), hydroxylamine hydrochloride (1.06 g, 15.2 mmol), and sodium acetate (1.25 g, 15.2 mmol) in ethanol (36 mL) was heated to 36° C. for 2 h. The reaction was then concentrated and the residue was dissolved in EtOAc (200 mL). The organic phase was washed with water (2×20 mL), brine, dried (MgSO4), and concentrated to give crude ethyl 4-(1-(hydroxyimino)-2-methylpropyl)benzoate as a slight-yellow solid. LC-MS: (FA) ES+ 236.

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe organic phase was washed with water (2×20 mL), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3a723b3af7f45f0bcc9c2c4c526fb84
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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