Formaldehyde → N-phenylmethoxymethanimine

HRID 615311Notes

Reaction equation

HRID 615311 reaction equation
[CH2:1]=O.Cl.[CH2:4]([O:11][NH2:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>O>[CH2:4]([O:11][N:12]=[CH2:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 561610N-phenylmethoxymethanimine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

37% Formaldehyde (11.7 mL) was added to a slurry of benzyloxyamine hydrochloride (25.0 g, 0.156 mole) in 50 mL H2O. NaOH (6.3 g) in 25 mL H2O was then added over 20 minutes. The temperature rose to 40°. After stirring 2 hours, the reaction mixture was extracted 1×100 mL and 2×25 mL of ether. The ether extracts were combined, washed 2×50 mL saturated NaHCO3 and then 2×50 mL brine, dried and evaporated to yield title product as an oil, 20.0 g b.p. 195.5°.

Workup

  1. customrose to 40°
  2. extractionthe reaction mixture was extracted 1×100 mL and 2×25 mL of ether
  3. washwashed 2×50 mL saturated NaHCO3
  4. dry with material2×50 mL brine, dried
  5. customevaporated

Sources & evidence

ORD record
ord-e131f603a37c4381982b537df0273337
Source dataset
uspto-grants-1985_02
Patent number
US04499017

Reaction notes

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