Hydroxylamine HCl → (NE)-N-[(2-methyl-5-phenylmethoxyphenyl)methylidene]hydroxylamine

HRID 1486845Notes

Reaction equation

HRID 1486845 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[OH:19][NH3+:20].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13](/[CH:14]=[N:20]/[OH:19])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 600256215-(Benzyloxy)-2-methylbenzaldehyde

Product 1

HCID 118292784(NE)-N-[(2-methyl-5-phenylmethoxyphenyl)methylidene]hydroxylamineYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(benzyloxy)-2-methylbenzaldehyde (15.9 g), hydroxyl ammonium chloride (5.37 g), sodium bicarbonate (6.49 g), and ethanol (150 mL) was stirred at room temperature for 6 hours. The precipitate was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (16.7 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c599fea1486949f390b69f224beff728
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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