Sodium Hydroxide → 3,3-Diphenylpropanal

HRID 886810Notes

Reaction equation

HRID 886810 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]=[O:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 299083,3-DiphenylpropanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 110746643,3-DiphenylpropanalYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.69 mL (23.55 mmol, 1 eq) of 3,3-diphenyl-1-propanol are dissolved in 100 mL of CH2Cl2 under Ar. 10.5 g (24.73 mmol, 1.05 eq) of Dess Martin Periodinane are added and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluant: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%).

Workup

  1. washThe organic phase is washed with 2 M sodium hydroxide (twice), with water (twice),
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude reaction product
  6. customAn oil which crystallises in the form of a white product
  7. customis recovered (4.76 g, yield=96%)

Sources & evidence

ORD record
ord-05d365d6e6474a10b4eefcd0de5f1634
Source dataset
uspto-grants-2012_08
Patent number
US08247412B2

Reaction notes

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