3,3-Dimethylbutanal → (Z)-2-(4-chloro-phenyl)-5,5-dimethyl-hex-2-enenitrile

HRID 1806720Notes

Reaction equation

HRID 1806720 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH:14]=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:14]/[CH2:13][C:12]([CH3:17])([CH3:16])[CH3:11])/[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 2415824-Chlorobenzyl cyanideHCID 10942334Sodium Methoxide

Product 1

HCID 59249443(Z)-2-(4-chloro-phenyl)-5,5-dimethyl-hex-2-enenitrileYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chlorobenzyl cyanide (4.5 g, 30 mmol) was reacted with 3,3-dimethyl-butyraldehyde (Aldrich) (3 g, 30 mmol), methanolic solution (25 wt %) of sodium methoxide (7 mL, 30 mmol) in methanol (130 mL) at room temperature for 3 h to give (Z)-2-(4-chloro-phenyl)-5,5-dimethyl-hex-2-enenitrile as a colorless oil (5 g, 71%).

Sources & evidence

ORD record
ord-739c73b1c2884616a1b069b545567569
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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