Hydroxyamine hydrochloride → HCID 85545547, compound

HRID 2352643Notes

Reaction equation

HRID 2352643 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[CH:10][CH:11]=O)=[CH:7][C:6]=1[O:15][CH3:16])(=[O:3])[CH3:2].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>CO>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[CH:10][CH:11]=[N:18][OH:19])=[CH:7][C:6]=1[O:15][CH3:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 30176002-Methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate

Product 1

HCID 85545547HCID 85545547, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Acetoxy-3-methoxycinnamaldehyde (2.0 g, 9.1×10-3M) is dissolved in methanol 100 ml) and cooled to 0° C. with an ice/water bath. Hydroxylamine hydrochloride (0.8 g, 1.2×10-2M) is added with sodium acetate (0.97 g, 1.2×10-2M) and stirred for one hour. The reaction mixture is concentrated to near dryness, and redissolved in ethyl acetate (150 ml). The residual organics are washed twice with water dried over sodium sulfate, filtered, evaporated to dryness, and chromatographed on flash silica using hexane:ethyl acetate 3:1 to afford 1.45 g of 4-acetoxy-3-methoxycinnamaldehyde oxime in 68% yield; mp=72°-74° C.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionredissolved in ethyl acetate (150 ml)
  3. washThe residual organics are washed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customchromatographed on flash silica

Sources & evidence

ORD record
ord-60e57d1b5e0d4ed1b058ca0bd5adea28
Source dataset
uspto-grants-1989_10
Patent number
US04877881

Reaction notes

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