1-Benzyloxy-4-phenyl-butan-2-ol → 1-Benzyloxy-4-phenyl-butan-2-one

HRID 8189

Reaction equation

HRID 8189 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:8][CH2:9][C:10](=[O:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 133473711-Benzyloxy-4-phenyl-butan-2-olHCID 178418287HCID 178418287, compound

Product 1

HCID 219927821-Benzyloxy-4-phenyl-butan-2-oneYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyloxy-4-phenyl-butan-2-ol, (8.4 g, 32.8 mmol) in dichloromethane (400 mL) is added a mixture of pyridinium chlorochromate (14.1 g, 65.6 mmol) with SiO2 (14 g) and stirred for 3 h at room temperature. The mixture is filtered through a pad of SiO2 and concentrated to provide the title compound 5.7 g (68%) as a colorless liquid.

Workup

  1. filtrationThe mixture is filtered through a pad of SiO2
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-16f69d03a0444212bf99c7b0fcc0694b
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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