Water → Methyl 3-cyano-4-hydroxybenzoate

HRID 1942599Notes

Reaction equation

HRID 1942599 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.CC(=O)OCC.O.[CH3:20][N:21](C)C=O>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([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:21]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

To a solution of methyl 4-hydroxy-3-iodobenzoate (2.78 g) and Zn(CN)2 (1.409 g) in N,N-dimethylformamide (DMF) (30 mL) stirred under nitrogen at room temperature was added Pd(Ph3P)4 (1.155 g). The reaction mixture was stirred at 140° C. for 12 h. After cooling the reaction, EA (100 mL) and water (40 mL) were added to the solution. After filtration, the filtrate was washed with water and brine, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography to afford methyl 3-cyano-4-hydroxybenzoate (D21) (1.3 g) as a white solid. MS (ES): C9H7NO3 requires 177. found 178.0 (M+H+).

Workup

  1. temperatureAfter cooling
  2. additionwere added to the solution
  3. filtrationAfter filtration
  4. washthe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f581a5970dcf461cb0a2ec89a511dff0
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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