Acetic Acid → 3-(2,2-Dichlorovinyloxy)mandelonitrile

HRID 1578125Notes

Reaction equation

HRID 1578125 reaction equation
[Cl:1][C:2]([Cl:13])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].[C-:14]#[N:15].[Na+].C(O)(=O)C>C(O)C.O>[Cl:1][C:2]([Cl:13])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]([OH:9])[C:14]#[N:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 134899763-(2,2-Dichlorovinyloxy)-benzaldehyde

Product 1

HCID 205689253-(2,2-Dichlorovinyloxy)mandelonitrileYield 91.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To the combined solutions of 30 g of 3-(2,2-dichlorovinyloxy)benzaldehyde in 320 ml of ethanol and 15 g of NaCN in 30 ml water are added 39 ml of acetic acid dropwise at 0°-5° C. in the course of 1 hour. The resultant solution is stirred for 1 hour at 20°-25° C. and subsequently diluted with 1000 ml of H2O. The product is extracted with toluene, washed and evaporated, to yield 31 g of 3-(2,2-dichlorovinyloxy)mandelonitrile. The crude product can be processed without further purification.

Workup

  1. extractionThe product is extracted with toluene
  2. washwashed
  3. customevaporated

Sources & evidence

ORD record
ord-21b8b3251cad4b1fb62d4ff6b4e70341
Source dataset
uspto-grants-1981_09
Patent number
US04291056

Reaction notes

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