5-Bromovanillin → Benzonitrile, 5-formyl-2-hydroxy-3-methoxy-

HRID 428824

Reaction equation

HRID 428824 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>>[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

3

Reactant 2

HCID 180995-BromovanillinHCID 31374Dimethylacetamide

Product 1

HCID 18359065Benzonitrile, 5-formyl-2-hydroxy-3-methoxy-

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 extracted 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

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. additionthe mixture was poured over ice
  4. extractionextracted with an ethyl acetate—methanol mixture (90-10)
  5. washThe organic phase was washed
  6. customdried

Sources & evidence

ORD record
ord-8dd3c32657b642bf9e071ca64ad18909
Source dataset
uspto-grants-2001_11
Patent number
US06313305B1

Linked notes

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