Diethyl Ether → HCID 58707290, compound

HRID 1910627Notes

Reaction equation

HRID 1910627 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-21e821e2805e4a48b56e179f9c0a1f4c
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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