Water → 4-Formyl-3-methoxybenzonitrile

HRID 1951374Notes

Reaction equation

HRID 1951374 reaction equation
I([O-])(=O)(=O)=O.[Na+].[C:7]([C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=C/C(OC(C)(C)C)=O)=[C:11]([O:24][CH3:25])[CH:10]=1)#[N:8].[OH2:26]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C1COCC1.[Os](=O)(=O)(=O)=O>[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][C:11]=1[O:24][CH3:25])=[O:26]

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 59186923HCID 59186923, compound

Product 1

HCID 166592514-Formyl-3-methoxybenzonitrile

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

79 g (370 mmol) of sodium metaperiodate are added in portions to a vigorously stirred solution of 48 g (185 mmol) of tert-butyl (2E)-3-(4-cyano-2-methoxyphenyl)acrylate, 207 mg (0.81 mmol) of osmium tetroxide and 1.4 g (6.14 mmol) of benzyltriethylammonium chloride in 750 ml of water/THF (2:1), keeping the reaction temperature below 30° C. The solution is stirred at RT for a further 1 h. Water (2000 ml) is added and the mixture is then filtered. The remaining solid is dissolved in ethyl acetate, and the solution is washed with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is stirred with petroleum ether. 21.18 g (71% of theory) of the title compound are obtained as a white solid.

Workup

  1. customthe reaction temperature below 30° C
  2. filtrationthe mixture is then filtered
  3. dissolutionThe remaining solid is dissolved in ethyl acetate
  4. washthe solution is washed with saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated
  7. stirringThe residue is stirred with petroleum ether

Sources & evidence

ORD record
ord-4f0b5190e6564fefadb6829d304904fd
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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