(4'-Methoxy[1,1'-biphenyl]-4-yl)methanol → 4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde

HRID 1072704Notes

Reaction equation

HRID 1072704 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 1051637(4'-Methoxy[1,1'-biphenyl]-4-yl)methanol

Product 1

HCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehydeYield 92.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of 4-(4′-methoxyphenyl)benzylalcohol (1.20 g, 5.60 mmol), manganese dioxide (2.0 g) and tetrahydrofuran (25 ml) was stirred at room temperature for 72 hours. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate:tetrahydrofuran=5:1:1) to give the object compound (1.1 g) as colorless crystals. Melting point: 99-100° C.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate:tetrahydrofuran=5:1:1)

Sources & evidence

ORD record
ord-b815034f81cd49648edc396c25a1dd2e
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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