4-Methylbenzaldehyde → HCID 19475, compound

HRID 1576970Notes

Reaction equation

HRID 1576970 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[OH-].[Na+]>O.C(O)C>[CH3:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:2][OH:3])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 19475HCID 19475, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride (41.7 g) in 70 ml of water was added to a solution of 36.1 g of 4-methylbenzaldehyde in 180 ml of absolute ethanol. A solution of 18 g of sodium hydroxide in 36 ml of water was added in portions during 5 to 10 minutes. The reaction mixture was then heated to boiling and filtered hot, and the filtrate was cooled in a dry ice-acetone bath. Water was added to the cooled filtrate until solid product precipitated. The solid was separated by filtration, air-dried overnight, and recrystallized from hexane to give 27.9 g of 4-methylbenzaldoxime, m.p. 73°-77°.

Workup

  1. temperatureThe reaction mixture was then heated
  2. filtrationfiltered hot
  3. temperaturethe filtrate was cooled in a dry ice-acetone bath
  4. additionWater was added to the cooled filtrate until solid product
  5. customprecipitated
  6. customThe solid was separated by filtration
  7. customair-dried overnight
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-94efb2673a034582898c30e45f5895b4
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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