1-(4-Bromo-3-methylphenyl)ethanol → 1-(4-Bromo-3-methylphenyl)ethanone

HRID 1500959Notes

Reaction equation

HRID 1500959 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:21])[CH3:20])=[CH:15][C:14]=1[CH3:22]>ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][C:14]=1[CH3:22]

Participants

4

Reactant 2

HCID 790169431-(4-Bromo-3-methylphenyl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 3471241-(4-Bromo-3-methylphenyl)ethanoneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (48 g, 223 mmol) was added to a solution of 1-(4-bromo-3-methylphenyl)ethanol (31.9 g, 148 mmol) in dichloromethane (800 mL). The mixture was stirred at room temperature for 2 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1) to give 1-(4-bromo-3-methylphenyl)ethanone (27.3 g, 87%).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1)

Sources & evidence

ORD record
ord-2810b3904ff94b9bb84dea21a46d0f3b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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