Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate

HRID 1697823Notes

Reaction equation

HRID 1697823 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-2a620dd2a5e94cae90c5e8263571992c
Source dataset
uspto-grants-2012_04
Patent number
US08163919B2

Reaction notes

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