Sodium Cyanide → 4,4'-Dimethoxybenzoin

HRID 1425806Notes

Reaction equation

HRID 1425806 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[C-]#N.[Na+]>CCO.O>[OH:8][CH:7]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:7]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:8]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 954154,4'-DimethoxybenzoinYield 65.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 4-methoxybenzaldehyde (2 g, 14.6 mmol) in EtOH (50 mL) was added a solution of NaCN (0.8 g, 16.3 mmol) in water (5 mL) and the reaction mixture was refluxed for 16 h. The reaction mixture was diluted with water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered and then concentrated in vacuo to yield a crude material which was purified via silica gel column chromatography eluting with 40% EtOAc in hexanes to afford 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone (1.3 g, 65%) as a solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 h
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a crude material which
  8. customwas purified via silica gel column chromatography
  9. washeluting with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-a63244faa55743b593c22cc52e4902b5
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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