Vanillin → 4-Hydroxy-3-methoxybenzonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=O.Cl.NO.C[N:16](C=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[C:6]#[N:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a 3-necked 500 mL round bottom flask equipped with a mechanical stirrer and a condenser, 3-methoxy-4-hydroxy benzoaldehyde (50.2 g, 0.33 mole), hydroxylamine hydrochloride (25.5 g, 0.37 mole), and N,N′-dimethylformamide (40 mL) were successively added at 25° C., followed by heating in an oil bath at 140° C. for 1 hour. The reaction mixture was allowed to cool to 85° C., and water (250 mL) was added to yield 3-methoxy-4-hydroxybenzonitrile. The reaction mixture was further cooled to 10° C. for a complete precipitation, and the resulting solid was then isolated by filtration and dried under reduced pressure to yield a product as an off-white solid with a yield of 95% and a purity of higher than 99% as indicated by HPLC analysis.
Workup
- customTo a 3-necked 500 mL round bottom flask equipped with a mechanical stirrer and a condenser
- temperatureto cool to 85° C.
Sources & evidence
- ORD record
- ord-88cab538010f40b4940cbdae109cae2b
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790977B2
Reaction notes
Loading…