Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate

HRID 222912Notes

Reaction equation

HRID 222912 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-8a185fc524674c4b8bfe9860a98934af
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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