Triacetoxyperiodinane → 4-Benzyloxyphenylacetaldehyde

HRID 62855

Reaction equation

HRID 62855 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=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>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]=[O:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 3017260p-(Benzyloxy)phenethyl alcohol

Product 1

HCID 114134894-BenzyloxyphenylacetaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Benzyloxy-phenyl)-ethanol (0.64 g, 2.80 mmol) obtained in Step B was dissolved in DCM (10 mL), and Dess-Martin periodinane (2.38 g, 5.60 mmol) was added thereto. The reactant was stirred at room temperature for 2 hours, diluted with DCM, and washed with Na2S2O3.5H2O aqueous solution. The remained organic solution was dried with MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.50 g, 79%).

Workup

  1. washwashed with Na2S2O3.5H2O aqueous solution
  2. dry with materialThe remained organic solution was dried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-c47e3fb21b794da6acbfe7bae25b1ab3
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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