Sodium Cyanide → Methyl 3-cyano-4-hydroxybenzoate

HRID 730360Notes

Reaction equation

HRID 730360 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-ead1f593f9e44093a1f3b7ba30b2e522
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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