Sodium Bicarbonate → (2-Chloro-4-nitrophenyl)acetaldehyde

HRID 1019732Notes

Reaction equation

HRID 1019732 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH:12]=[O:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 226719422-(2-Chloro-4-nitrophenyl)ethanol

Product 1

HCID 54570839(2-Chloro-4-nitrophenyl)acetaldehydeYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-N-benzodioxol-3(1H)-one (Dess-Martin periodinane) (25.24 g, 59 mmol) in DCM (92 mL) was added a solution of 2-(2-chloro 4-nitro-phenyl)ethanol (10 g, 49 mmol) in DCM (30 mL) at RT. The reaction mixture was stirred for 3 hours at RT. After completion of reaction, sodium bicarbonate solution was added and the mixture was stirred for 15 minutes. The separated organic layer was washed with water (2×50 mL), dried (Na2SO4) and the solvent removed under reduced pressure to afford the title compound (9.5 g, 95%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 15 minutes
  3. washThe separated organic layer was washed with water (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3db82f38a508489ebda8c1fd3d104c4f
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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