Water → 2-(3,4-Dimethoxyphenyl)-2-(propan-2-yl)pentanedinitrile

HRID 2309820Notes

Reaction equation

HRID 2309820 reaction equation
[CH:1]([CH:4]([C:15]#[N:16])[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].CO[CH2:19][CH2:20][C:21]#[N:22].C[O-].[Na+].O>CN(C)C=O>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([C:4]([C:15]#[N:16])([CH:1]([CH3:3])[CH3:2])[CH2:19][CH2:20][C:21]#[N:22])[CH:14]=[CH:13][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 610323-MethoxypropionitrileHCID 893962-(3,4-Dimethoxyphenyl)-3-methylbutanenitrileHCID 10942334Sodium Methoxide

Product 1

HCID 136282682-(3,4-Dimethoxyphenyl)-2-(propan-2-yl)pentanedinitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

438.4 g (2 mol) of α-isopropyl-veratryl cyanide and 204.2 g (2.4 mol) of 3-methoxypropionitrile are dissolved in 400 ml of dimethylformamide, 36 ml of a 5.5 molar solution of sodium methylate are added, and the mixture is heated to 85° C. for 1/2 hour. After cooling, water is added to the reaction mixture and the reaction product separates by crystallisation. Recrystallised from methanol/water, the product melts at 97° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction product separates by crystallisation
  3. customRecrystallised from methanol/water

Sources & evidence

ORD record
ord-19da2e56868341a7839664ea9f1d4fe6
Source dataset
uspto-grants-1987_09
Patent number
US04697035

Reaction notes

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