Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate

HRID 1785061Notes

Reaction equation

HRID 1785061 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.[H-].[Na+].[CH3:15][N:16](C=O)C>>[C:15]([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:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Procedure

A solution of compound 2 (6.46 g, 24.1 mmol) in DMF (30 mL) was treated with sodium hydride (1.94 g of 60% dispersion in mineral oil, 48.6 mmol) portionwise at room temperature. The resulting mixture was stirred at room temperature for 16 hours and then partitioned between water (100 mL) and EtOAc (350 mL). The layers were separated, and the organic layer was washed with water (4×150 mL). The organic phase was dried (Na2SO4) and concentrated to a white solid. Compound 3 (5.56 g, 24.0 mmol, quantitative yield) was dried under high vacuum and characterized using 1H NMR. It was used in the following step without further purification.

Workup

  1. custompartitioned between water (100 mL) and EtOAc (350 mL)
  2. customThe layers were separated
  3. washthe organic layer was washed with water (4×150 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-9e0a544a12ff4aa98f2559e51de7b16d
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

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