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

HRID 2393932

Reaction equation

HRID 2393932 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) δ 2.16 (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-4c735c37153b4e0fb2f21dae9038d228
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Linked notes

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