(2-(Benzyloxy)-4-fluorophenyl)methanol → 2-(Benzyloxy)-4-fluorobenzaldehyde

HRID 1072062Notes

Reaction equation

HRID 1072062 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58882932(2-(Benzyloxy)-4-fluorophenyl)methanol

Product 1

HCID 106809572-(Benzyloxy)-4-fluorobenzaldehydeYield 59%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 2-(benzyloxy)-4-fluorobenzyl alcohol (6.54 g) and manganese(IV) oxide (9.04 g) in chloroform (70 ml) was refluxed and stirred for 2 hr. The insoluble material was removed by filtration and washed with chloroform. The filrate was evaporated and the residue (6.7 g) was chromatographed over silica gel (90 g) eluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane to give a colorless oil of 2-(benzyloxy)-4-fluorobenzaldehyde (3.8 g, 59%).

Workup

  1. temperaturewas refluxed
  2. customThe insoluble material was removed by filtration
  3. washwashed with chloroform
  4. customThe filrate was evaporated
  5. customthe residue (6.7 g) was chromatographed over silica gel (90 g)
  6. washeluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane

Sources & evidence

ORD record
ord-52240e8b98264899b29f497eab14eebe
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

Loading…