Formaldehyde → HCID 69433836, compound

HRID 1294453Notes

Reaction equation

HRID 1294453 reaction equation
Cl.[C:2]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][O:9][NH2:10])=[C:6]([O:13][CH2:14][CH3:15])[CH:5]=1)#[N:3].[CH3:16][OH:17].C=O>O>[C:2]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][O:9][NH2:10])=[C:6]([O:13][CH2:14][CH3:15])[CH:5]=1)#[N:3].[CH2:16]=[O:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 887MethanolHCID 69434226O-(4-cyano-2-ethoxybenzyl)hydroxyamine hydrochloride

Product 1

HCID 69433836HCID 69433836, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

O-(4-cyano-2-ethoxybenzyl)hydroxyamine hydrochloride (19-1, 2.7 g, 0.012 mol), methanol (20 ml) and water (20 ml) were charged, and a 36% formaldehyde aqueous solution was added to this, and the mixture was stirred at room temperature for 2.0 hours. Water was added to the mixture and the mixture was extracted with ethyl acetate. The resulted ethyl acetate layer was dried over anhydrous magnesium sulfate, then, the solvent was distilled off under reduce pressure. This was purified by silica gel column chromatography using hexane/ethyl acetate system, to obtain O-(4-cyano-2-ethoxybenzyl)hydroxyamine-formaldehyde derivative (3-1a, 2.2 g, yield 96%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe resulted ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThis was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b635086fdb4b4c5d979b53b05dc73ddb
Source dataset
uspto-grants-2007_07
Patent number
US07241625B2

Reaction notes

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