2,6-Dichlorobenzaldehyde → Dichlobenil

HRID 225039

Reaction equation

HRID 225039 reaction equation
S(O)(O)(=O)=O.[NH2:6]O.O.O.O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH:26]=O>C(O)(=O)C>[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[C:26]#[N:6]

Participants

6

Reactant 4

HCID 67372,6-DichlorobenzaldehydeHCID 7918Acetic AnhydrideHCID 159255Hydroxylamine, sulfate (1:1)HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 3031DichlobenilYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.7 g of hydroxylamine sulphate, 7 g of sodium acetate trihydrate, 17 g of acetic anhydride, 5 ml of acetic acid and 4.5 g of 2,6-dichlorobenzaldehyde was heated at reflux for 34 hours. Cooling, filtration and washing with water gave 2.7 g of pure 2,6-dichlorobenzonitrile. Stripping of the filtrate gave an additional 1 gram of pure 2,6-dichlorobenzontirile thus producing an overall yield of 84%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 34 hours
  3. temperatureCooling
  4. filtrationfiltration
  5. washwashing with water

Sources & evidence

ORD record
ord-81797b614c9448d08d64a83ef37f7603
Source dataset
uspto-grants-1980_11
Patent number
US04235807

Linked notes

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