Isoamyl Nitrite → 2-hydroxyimino-2-(4-methoxyphenyl)acetonitrile

HRID 962376Notes

Reaction equation

HRID 962376 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[N:13](OCCC(C)C)=[O:14].[OH-].[Na+]>O.C1(C)C(C)=CC=CC=1.CO>[OH:14][N:13]=[C:10]([C:11]#[N:12])[C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 8053Isoamyl NitriteHCID 14798Sodium HydroxideHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 5360545Sodium

Product 1

HCID 43981912-hydroxyimino-2-(4-methoxyphenyl)acetonitrileYield 80.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

64.5 g of methanol, 365 g of xylene, 80 g of sodium hydroxyde (2 mol) and 147 g (1 mol) of 4-methoxyphenylacetonitrile are charged to a reactor. Then 125 g (1.07 mol) of isopentyl nitrite are added dropwise at 40° C. over 2 hours. The reaction mixture is stirred initially for 2 hours at this temperature and the n for 20 hours at room temperature. Afterwards the reaction mixture is diluted with water to form an emulsion and the pH is adjusted to 14 with aqueous sodium hydroxide and the organic phase is separated. The aqueous phase is acidified with hydrochloric acid and the product is extracted with ether. The ether phase is dried and the ether is stripped off. Recrystallisation from toluene gives 142 g of α-hydroxyimino-4-methoxy-benzylcyanide, corresponding to a yield of 80.6% of theory.

Workup

  1. waitthe n for 20 hours at room temperature
  2. customto form an emulsion
  3. customthe organic phase is separated
  4. extractionthe product is extracted with ether
  5. dry with materialThe ether phase is dried
  6. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-da25d505a29a43a4b3348da8f66e621b
Source dataset
uspto-grants-1998_06
Patent number
US05759740

Reaction notes

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