Formaldehyde → N-phenylmethoxymethanimine

HRID 530054Notes

Reaction equation

HRID 530054 reaction equation
[OH-].[Na+].Cl.[CH2:4]([O:11][NH2:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]=O>O.C1(C)C=CC=CC=1>[CH2:4]([O:11][N:12]=[CH2:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 561610N-phenylmethoxymethanimineYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A NaOH (1.25 g, 31.32 mmol) solution in water (6 mL) was added to the mixture of O-benzyl-hydroxylamine hydrochloride (5.00 g, 31.32 mmol) and formaldehyde (˜37 wt. % in H2O) (2.3 mL, 31.32 mmol) in toluene (40 mL). The reaction mixture was stirred at room temperature for 1 h. After this time, the organic phase was separated and the water phase was extracted with dichloromethane (3×30 mL). The combined organic phases were dried over Na2SO4, and concentrated in vacuo to yield formaldehyde O-benzyl-oxime (LI, 4.15 g, 98%). 400 MHz 1H NMR (CDCl3, ppm) 7.40-7.29 (5H, m), 7.09 (1H, d, J=8.2 Hz), 6.47 (1H, d, J=8.2 Hz), 5.14 (2H, s).

Workup

  1. customAfter this time, the organic phase was separated
  2. extractionthe water phase was extracted with dichloromethane (3×30 mL)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73c24bfb9a944b2599e18c6dc4069f94
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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