3-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-ol → 3-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehyde

HRID 400629Notes

Reaction equation

HRID 400629 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][OH:11])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]([CH3:12])([CH3:13])[CH2:9][CH:10]=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 578097383-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 578098963-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol (3.30 g, 15.5 mmol) in 40 mL of dichloromethane was treated with pyridinium chlorochromate (4.2 g, 19.5 mmol) portionwise over 5 minutes. The mixture was stirred for 3 hours, filtered through pad of CELITE® filter aid and the pad was wash with hexanes. The filtrate was concentrated in vacuo. Chromatography on SiO2 (30% to 50% dichloromethane in hexanes, gradient) gave 2.5 g of 3-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehyde as an oil (77% yield).

Workup

  1. filtrationfiltered through pad of CELITE®
  2. filtrationfilter aid
  3. washthe pad was wash with hexanes
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2e6ee3903548437f9e3fda8ed88e5101
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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