Triacetoxyperiodinane → 2-(4-Bromo-2,6-dimethylphenyl)acetaldehyde

HRID 735633Notes

Reaction equation

HRID 735633 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([CH2:31][CH2:32][OH:33])=[C:26]([CH3:34])[CH:25]=1>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[C:26]([CH3:34])[C:27]([CH2:31][CH:32]=[O:33])=[C:28]([CH3:30])[CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 578427022-(4-Bromo-2,6-dimethylphenyl)ethanol

Product 1

HCID 578426542-(4-Bromo-2,6-dimethylphenyl)acetaldehydeYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (5.2 g, 12.5 mmol) was added portionwise to a solution of 32B (2.6 g, 11.4 mmol) in CH2Cl2 (60 mL) at 0° C. and the mixture was stirred at ambient temperature for 2 h. The reaction mixture was filtered and stirred with NaOH (1.0 M, 40 mL) for 10 min. The organic layer washed with brine, dried over Na2SO4 and concentrated to yield 53A (2.6 g, 99%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.24 (s, 6 H) 3.71 (d, J=1.77 Hz, 2 H) 7.20-7.20 (m, 2 H) 9.66 (t, J=1.89 Hz, 1 H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. stirringstirred with NaOH (1.0 M, 40 mL) for 10 min
  3. washThe organic layer washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cce9e40bc9fe4c8ba223b6bd709e72a9
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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