(4-(5-Methyl-furan-2-ylmethyl)-phenyl)-methanol → 4-(5-Methyl-furan-2-ylmethyl)-benzaldehyde

HRID 77909Notes

Reaction equation

HRID 77909 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].ClCCl>[CH3:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59255234(4-(5-Methyl-furan-2-ylmethyl)-phenyl)-methanol

Product 1

HCID 592552654-(5-Methyl-furan-2-ylmethyl)-benzaldehydeYield 29.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-(5-methyl-furan-2-ylmethyl)-phenyl)-methanol (350 mg, 1.7 mmol) obtained in Manufacturing Example 46-1-2 and dichloromethane (10 mL) was added manganese dioxide (3.5 g, 4.7 mmol) at room temperature, which was stirred overnight at room temperature. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:6) to obtain the title compound (100 mg, 29%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:6)

Sources & evidence

ORD record
ord-608faaa948eb44b1a8e2ca6930a0f375
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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