Ethyl Acetate → Benzonitrile, 5-formyl-2-hydroxy-3-methoxy-
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].C[C:14]([N:16](C)C)=O.C(OCC)(=O)C>CO>[CH:5]([C:4]1[CH:3]=[C:2]([C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=1)[C:14]#[N:16])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 23.1 g of 3-bromo-4-hydroxy-5-methoxy benzaldehyde, 9.3 g of cuprous cyanide and 140 ml of dimethyl acetamide (DMA) was refluxed for 2 hours with stirring. After cooling, the mixture was poured over ice and extract&d with an ethyl acetate--methanol mixture (90-10). The organic phase was washed and dried and the solvents were eliminated to obtain 18 g of crude product, which was used as is for the following step. It melted at 180° C.
Workup
- temperaturewas refluxed for 2 hours
- temperatureAfter cooling
- washThe organic phase was washed
- customdried
Sources & evidence
- ORD record
- ord-d03242f3367b42868367bf19135dae30
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05728828
Reaction notes
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