Formaldehyde → Formanilide

HRID 1414449Notes

Reaction equation

HRID 1414449 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[O:9].OO>[O-][W]([O-])(=O)=O.[Na+].[Na+].O>[CH:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 784Hydrogen PeroxideHCID 6115Aniline

Product 1

HCID 7671Formanilide

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 962WaterSolvent

Procedure

18.6 g (0.2 mol) of aniline are introduced into 30 ml of water, followed by the dropwise addition with stirring of 20 g (0.2 mol) of a 30 % by weight aqueous formaldehyde solution. 0.2 g of sodium tungstate are then added, followed by the dropwise addition with continued stirring of 25 g of a 30 % by weight aqueous hydrogen peroxide solution. The temperature rises to about 60° to 70°C. The dark oil precipitated is taken up in about 30 ml of methylene chloride and the organic phase is separated off. The aqueous phase is repeatedly extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and subsequently subjected to fractional distillation in vacuo, giving 12.2 g (51 % of the theoretical yield) of formanilide boiling at 160° to 172°C/ 15 Torr.

Workup

  1. additionfollowed by the dropwise addition
  2. additionfollowed by the dropwise addition
  3. customrises to about 60° to 70°C
  4. customThe dark oil precipitated
  5. customthe organic phase is separated off
  6. extractionThe aqueous phase is repeatedly extracted with methylene chloride
  7. dry with materialThe combined organic phases are dried over sodium sulphate
  8. distillationsubsequently subjected to fractional distillation in vacuo
  9. customgiving 12.2 g (51 % of the

Sources & evidence

ORD record
ord-b538355861ea4f77ba7363be1774e72b
Source dataset
uspto-grants-1977_01
Patent number
US04001324

Reaction notes

Loading…