Triacetoxyperiodinane → 2,6-Bis-benzyloxybenzaldehyde

HRID 660619Notes

Reaction equation

HRID 660619 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[CH2:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[CH:23]=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68839928(2,6-Bis-benzyloxyphenyl)-methanol

Product 1

HCID 117268902,6-Bis-benzyloxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,6-bis-benzyloxyphenyl)-methanol (3.0 g) in methylene chloride (40 mL) is added Dess-Martin reagent (1.5 equivalents, 15% by weight in methylene chloride) and the mixture is stirred at RT for 30 min. Saturated NaHCO3 is added and the organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (7:1) as eluent to give the title compound as a reddish liquid.

Workup

  1. washthe organic phase is washed with water and brine
  2. dry with materialthen is dried over sodium sulfate
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-a45639c5e6e745cc90635ad59d477bc3
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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