Hydrochloric Acid → 4-Ethyl-2-hydroxy-5-nitrohexanenitrile

HRID 35575Notes

Reaction equation

HRID 35575 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([CH:6]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])[CH2:7][CH:8]=[O:9])[CH3:5].Cl>CCOCC>[CH2:4]([CH:6]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])[CH2:7][CH:8]([OH:9])[C:1]#[N:2])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 14329798HCID 14329798, compound

Product 1

HCID 143297994-Ethyl-2-hydroxy-5-nitrohexanenitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of sodium cyanide (4.5 g) and 3-ethyl-4-nitro-pentanal (7.5 g) in ether (50 ml) was added conc. hydrochloric acid (7.5 ml) at 0° C. with stirring. The resulting mixture was stirred at 0° C. for an hour, diluted with ether, washed successively with water and brine, dried over magnesium sulfate, and then evaporated to dryness in vacuo to give 4-ethyl-2-hydroxy-5-nitro-hexanenitrile (8.1 g).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for an hour
  2. washwashed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-66a7aa122b5746ad8ea94b1ebf054cfe
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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