Sodium Cyanide → 2-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

HRID 2309819Notes

Reaction equation

HRID 2309819 reaction equation
[CH:1]([CH:4](Cl)[C:5]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=1)([CH3:3])[CH3:2].[C-:16]#[N:17].[Na+].[OH-].[Na+]>O.C(N(CC)CC)C>[CH:1]([CH:4]([C:16]#[N:17])[C:5]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 13628267HCID 13628267, compound

Product 1

HCID 893962-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

457.4 g (2 mol) of α-isopropyl-veratryl chloride, 108 g (2.2 mol) of sodium cyanide, 10 mol-% of phase transfer catalyst, 100 ml of water and 800 ml of triethylamine are stirred together for 5 hours at 60° C. After the addition of 60 ml of 30% sodium hydroxide solution and 300 ml of water, the organic phase is separated off. After removal of the triethylamine by distillation, the residue is distilled in a fine vacuum. The distillate obtained is recrystallised from methanol/water.

Workup

  1. customthe organic phase is separated off
  2. customAfter removal of the triethylamine
  3. distillationby distillation
  4. distillationthe residue is distilled in a fine vacuum
  5. customThe distillate obtained
  6. customis recrystallised from methanol/water

Sources & evidence

ORD record
ord-486e08535f954360a1ee05ce9535d3bd
Source dataset
uspto-grants-1987_09
Patent number
US04697035

Reaction notes

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