Triacetoxyperiodinane → 3-(Benzyloxy)-2-methylbenzaldehyde

HRID 250639Notes

Reaction equation

HRID 250639 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH2:15][OH:16])[CH:12]=[CH:13][CH:14]=1)[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>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanol

Product 1

HCID 159481993-(Benzyloxy)-2-methylbenzaldehydeYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-benzyloxy-2-methyl-phenyl)-methanol (622, 627 mg, 2.75 mmol) in tetrahydrofuran (60 mL) was added Dess-Martin periodinane (2.9 g, 6.87 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. The reaction mixture was quenched with a solution of saturated sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (623, 0.55 g, 84%).

Workup

  1. customThe reaction mixture was quenched with a solution of saturated sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-1fcf1b7ef20e4204b2358d410a763833
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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