1,3-Diphenylpropan-1-ol → 1,3-Diphenyl-2-propanone

HRID 977229Notes

Reaction equation

HRID 977229 reaction equation
[C:1]1([CH:7](O)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]1([CH2:7][C:8](=[O:19])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2501291,3-Diphenylpropan-1-olHCID 131709961Jones' reagent

Product 1

HCID 75931,3-Diphenyl-2-propanoneYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of racemic 1,3-diphenyl-1-propanol (1.26 g; 5.94 mmol) was dissolved in 10 mL of acetone, and Jones reagent was added until persistence of the orange color. After stirring for 30 min, the reaction was quenched by adding 2 mL of 2-propanol. The solvent was decanted away from the precipitated solids, which were washed with ethyl acetate. The combined organic fractions were washed with 2×20 mL of water, dried and concentrated. The crude product was filtered through a plug of silica gel, eluting with 25% ethyl acetate/hexane, to obtain 1.07 g (86%) of 1,3-diphenylpropanone as a white crystalline solid, 1H NMR (360 Mhz; CDCl3): d 3.09 (t, 2H, J=8.1); 3.33 (t, 2H, J=8.1); 7.29 (m, 5H); 7.49 (m, 3H); 7.98 (m, 2H).

Workup

  1. customthe reaction was quenched
  2. additionby adding 2 mL of 2-propanol
  3. customThe solvent was decanted away from the precipitated solids, which
  4. washwere washed with ethyl acetate
  5. washThe combined organic fractions were washed with 2×20 mL of water
  6. customdried
  7. concentrationconcentrated
  8. filtrationThe crude product was filtered through a plug of silica gel
  9. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-163bcee8eaad4509a5b2cd32c70ecd7e
Source dataset
uspto-grants-1997_03
Patent number
US05614547

Reaction notes

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