Veratraldehyde → (3,4-Dimethoxyphenyl)(hydroxy)acetonitrile

HRID 1438174Notes

Reaction equation

HRID 1438174 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].OS([O-])=O.[Na+].[C-:18]#[N:19].[K+]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[C:18]#[N:19])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 8419VeratraldehydeHCID 9032Potassium CyanideHCID 23665763Sodium Bisulfite

Product 1

HCID 238239(3,4-Dimethoxyphenyl)(hydroxy)acetonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To 3,4-dimethoxybenzaldehyde (1.66 g, 10 mmol) in ethyl acetate (20 mL) was added NaHSO3 (5.2 g, 50 mmol) in water (20 mL), followed by potassium cyanide (3.26 g, 50 mmol) in water (20 mL). The mixture was stirred overnight at rt, then warmed to 50° C. for 6 h. The reaction was cooled to rt, diluted with ethyl acetate, and the layers were separated. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-50% ethyl acetate/hexanes) to provide 137A (1.25 g, 65%) and starting material (0.52 mg). LC-MS: 176.22 (M−H2O)+.

Workup

  1. temperaturewarmed to 50° C. for 6 h
  2. temperatureThe reaction was cooled to rt
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b212fcde10c24ebea4aeab74de5a85cb
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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