1-(Benzyloxy)propan-2-ol → 1-(Benzyloxy)propan-2-one

HRID 399104

Reaction equation

HRID 399104 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CN(C=O)C.O>[CH2:1]([O:8][CH2:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2959551-(Benzyloxy)propan-2-olHCID 178418287HCID 178418287, compound

Product 1

HCID 36912841-(Benzyloxy)propan-2-oneYield 78.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

3-Benzyoxypropan-2-ol 16 (40 g, 0.24 mol) was added to a suspension of pyridinium chlorochromate (155.2 g, 0.72 mol) in DMF (150 ml) at 25° C., stirred at 65° C. for 3 h, and then diluted with water (75 mL) (Step 14). The mixture was extracted with ether (2×50 mL) and the combined ether layers were washed with water (3×50 mL) dried (MgSO4) and the solvent removed by roto-evaporation. Distillation gave 31 g (77%) of 3-benzyloxypropan-2-one; 17 bp 104-106 (10 mm). 1H NMR (CDCl3) δ2.16 (s, 3H, CH3), 4.05 (s, 1H, OH), 4.59 (s, 2H, OCH2), 7.5 (s, 5H, phenyl).

Workup

  1. extractionThe mixture was extracted with ether (2×50 mL)
  2. washthe combined ether layers were washed with water (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by roto-evaporation
  5. distillationDistillation

Sources & evidence

ORD record
ord-071ec0f206a04182956109c495402c56
Source dataset
uspto-grants-1998_10
Patent number
US05817776

Linked notes

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