3,4,5-Trimethoxybenzaldehyde → 2-(Methoxymethyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enenitrile

HRID 414131Notes

Reaction equation

HRID 414131 reaction equation
C(#N)C=C.CO[CH2:7][O:8][CH3:9].COC1C=C(C=C(OC)C=1OC)C=O.C1N2CCN(CC2)C1.C(OC)=O.O[CH:37]([C:42]1[CH:47]=[C:46]([O:48][CH3:49])[C:45]([O:50][CH3:51])=[C:44]([O:52][CH3:53])[CH:43]=1)[C:38](=C)[C:39]#[N:40]>CO>[CH3:53][O:52][C:44]1[CH:43]=[C:42]([CH:37]=[C:38]([CH2:7][O:8][CH3:9])[C:39]#[N:40])[CH:47]=[C:46]([O:48][CH3:49])[C:45]=1[O:50][CH3:51]

Participants

8

Reactant 6

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 7855AcrylonitrileHCID 7865Methyl formateHCID 8020DimethoxymethaneHCID 9237DabcoHCID 15457786HCID 15457786, compound

Product 1

HCID 1113042-(Methoxymethyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

55 ml of acrylonitrile, 50 ml of dimethoxymethane, 100 g of 3,4,5-trimethoxybenzaldehyde and 30 g of DABCO are introduced into a 500 ml reactor fitted with a stirrer. After stirring for 25 hours, 50 g of methyl formate and 100 ml of methanol are added and the mixture is stirred at room temperature for more than 24 hours until the 3-hydroxy-2-methylene-3-(3,4,5-trimethoxyphenyl)propionitrile has disappeared; the 3-(3,4,5-trimethoxyphenyl)-2-methoxymethylacrylonitrile formed is isolated or reacted with sodium methylate, after removal of the volatile reactants and solvents, to give the acetal of the formula III.

Workup

  1. customfitted with a stirrer

Sources & evidence

ORD record
ord-b2d7b22bc1624072a81c2156bfca04ac
Source dataset
uspto-grants-1988_12
Patent number
US04789743

Reaction notes

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