Acetic Acid → 2,4-Dihydroxybenzonitrile

HRID 338801

Reaction equation

HRID 338801 reaction equation
C(O)(=O)C.[OH:5][C:6]1[C:13](O)=[CH:12]C=C[C:7]=1[CH:8]=[O:9].C([O-])(=O)C.[Na+].[N+:20]([CH2:23][CH3:24])([O-])=O>O.C(OCC)(=O)C>[OH:9][C:8]1[CH:7]=[C:6]([OH:5])[CH:13]=[CH:12][C:24]=1[C:23]#[N:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 905792,3-DihydroxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 30175202,4-DihydroxybenzonitrileYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an acetic acid (10 mL) solvent, a solution including 2,3-dihydroxybenzaldehyde (3.0 g, 21.7 mmol), sodium acetate (NaOAc) (3.54 g, 43.4 mmol), and nitroethane (3.24 g, 43.4 mmol) was refluxed for 8 hours. After cooling, the reaction mixture was distributed between ethyl acetate and water. Until a pH of the residual aqueous layer reached 8, an organic layer was washed with a saturated NaHCO3 solution. The organic layer was evaporated, the residual was purified by silica gel column chromatography using hexane and ethyl acetate (2:1) as a developer to obtain Compound 101a (1.88 g, 59%).

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. washan organic layer was washed with a saturated NaHCO3 solution
  4. customThe organic layer was evaporated
  5. customthe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-944a19531afa44a8ad9a48b7f41be7f9
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Linked notes

Loading…