Sodium Cyanide → Methyl 3-cyano-4-hydroxybenzoate

HRID 1697818Notes

Reaction equation

HRID 1697818 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.[C:13]([Cu])#[N:14].[C-]#N.[Na+]>CN(C=O)C>[C:13]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7])#[N:14]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 11346465Methyl 4-hydroxy-3-iodobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoateYield 101.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

28 g (0.1 mol) of methyl 4-hydroxy-3-iodobenzoate 2 dissolved in 100 mL of DMF was treated with 9.92 g (0.11 mol) of CuCN and 0.49 g (0.11 mol) of NaCN. The system was flushed with nitrogen after which the mixture warmed to 105° C. and stirred to 18 h. The mixture was allowed to cool to room temperature, and any precipitates were removed via filtration and washed with EtOAc. The combined organics were diluted with 200 mL of water and then extracted with EtOAc (2×200 mL). The combined layers were dried over sodium sulfate, filtered and evaporated to dryness. After drying under vacuum, the resulting 18 g (100% yield) of 3 was characterized by LCMS and HNMR.

Workup

  1. customThe system was flushed with nitrogen after which the mixture
  2. temperatureto cool to room temperature
  3. customany precipitates were removed via filtration
  4. washwashed with EtOAc
  5. additionThe combined organics were diluted with 200 mL of water
  6. extractionextracted with EtOAc (2×200 mL)
  7. dry with materialThe combined layers were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customAfter drying under vacuum

Sources & evidence

ORD record
ord-9015bcde65ba4fdb93cb24f4434e3447
Source dataset
uspto-grants-2012_04
Patent number
US08163919B2

Reaction notes

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