Acetonitrile → HCID 21794538, compound

HRID 2269700Notes

Reaction equation

HRID 2269700 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]#[N:21].C(#N)C>O>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=1[O:1][CH2:19][C:20]#[N:21])=[O:5]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 21794538HCID 21794538, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 2-hydroxy-4-methoxybenzaldehyde (9.50 g), potassium carbonate (17.3 g), bromoacetonitrile (11.2 g) and acetonitrile (100 ml) was stirred at room temperature for 12 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate), and then recrystallized from ethyl acetate-hexane to obtain the entitled compound (10.7 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-481ef0b581d6449c9e54b2589a22d346
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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