Sodium Cyanide → 4,4'-Dimethoxybenzoin

HRID 655385

Reaction equation

HRID 655385 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-ae33d721de5c472b8789893fd166cc0d
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Linked notes

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