Formaldehyde → N-phenylmethoxymethanimine

HRID 2408829Notes

Reaction equation

HRID 2408829 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]1(C)C=CC=CC=1.C=O.[OH-].[Na+]>O>[CH2:2]([O:9][N:10]=[CH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 14798Sodium Hydroxide2×HCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 561610N-phenylmethoxymethanimine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-Benzyl-hydroxylamine hydrochloride (125.0 g, 0.78 mol) was combined with toluene (400 mL) under nitrogen. The resulting slurry was cooled in an ice bath and formalin (37%, 75 mL) was added. A 50% solution of NaOH (70 mL) was added portionwise maintaining an internal temperature of not more than 35° C. After the addition of NaOH was complete, water (100 mL) was added and the reaction mixture was stirred at ambient temperature for 2.5 hours. The layers were then separated and the aqueous layer was extracted with toluene. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The resulting oil was distilled (65-70° C., 10 torr) to obtain formaldehyde O-benzyl-oxime. 1H NMR (400 MHz, CDCl3) δ ppm 5.12-5.13 (s, 2 H) 6.46 (d, J=8.23 Hz, 1 H) 7.08 (d, J=8.23 Hz, 1 H) 7.28-7.35 (m, 1 H) 7.36 (dd, J=4.19, 0.62 Hz, 4 H).

Workup

  1. temperatureThe resulting slurry was cooled in an ice bath
  2. temperaturemaintaining an internal temperature of not more than 35° C
  3. customThe layers were then separated
  4. extractionthe aqueous layer was extracted with toluene
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. distillationThe resulting oil was distilled (65-70° C., 10 torr)

Sources & evidence

ORD record
ord-e9282b19895f4e9589b7915c68243cde
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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