Methanol → alpha-(3,4-Dimethoxy-benzal)-beta-methoxy-propionitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[CH3:13][O:14][CH2:15][CH2:16][C:17]#[N:18].CO.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[C:16]([CH2:15][O:14][CH3:13])[C:17]#[N:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
A mixture of 200 g (1.20 mole) of 3,4-dimethoxy-benzaldehyde, 150 g (1.75 mole) of β-methoxy-propinitrile, 260 ml of methanol and 10 g of a 55% methanolic potassium hydroxide solution is stirred at 60°-62° C. for 8 hours, whereupon the reaction mixture is cooled to 30° C., and 170 g of a 55% methanolic potassium hydroxide solution are added dropwise. The reaction mixture is stirred for 5 hours and diluted with 1000 ml of water. The precipitated crystalline product is filtered, washed with methanol and water. Thus 280 g of α-(3,4-dimethoxy-benzal)-β-methoxy-propionitrile are obtained, yield 85%, mp.: 82°-83° C.
Workup
- stirringThe reaction mixture is stirred for 5 hours
- filtrationThe precipitated crystalline product is filtered
- washwashed with methanol and water
Sources & evidence
- ORD record
- ord-ef0842d94a3849718e1bcac0753f13a2
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04873249
Reaction notes
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