Diethyl Ether → HCID 58707290, compound

HRID 2426069Notes

Reaction equation

HRID 2426069 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58707309HCID 58707309, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58707290HCID 58707290, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(5-Fluoro-2-methoxy-3-methylphenyl)ethanol (1.3 g 7.13 mmol) in acetone (15 mL) at room temperature was added pyridinium chlorochromate (3.8 g, 17.64 mmol). The reaction was stirred for 3 hours, diethyl ether was added (30 mL). The resultant sludge was filtered through celite. The organic phase was dried over Na2SO4, filtered over silica gel, and concentrated to the crude compound which was purified by silica gel column (20% ethyl acetate in hexanes) to afford 1-(5-fluoro-2-methoxy-3-methylphenyl)ethanone (1.2 g, 98%): 1H NMR (400 MHz, CDCl3): δ 7.18 (dd, 1H), 7.05 (dd, 1H), 3.63 (s, 3H), 2.61 (s, 3H), 2.39 (s, 3H).

Workup

  1. filtrationThe resultant sludge was filtered through celite
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered over silica gel
  4. concentrationconcentrated to the crude compound which
  5. customwas purified by silica gel column (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1aaea22d6eae4265b33967086033c7aa
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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