4-Fluoro-3-(phenylmethoxy)benzenemethanol → 3-(Benzyloxy)-4-fluorobenzaldehyde

HRID 2389340Notes

Reaction equation

HRID 2389340 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[CH:13][C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[F:15])[CH:16]=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 5614404-Fluoro-3-(phenylmethoxy)benzenemethanol

Product 1

HCID 5613353-(Benzyloxy)-4-fluorobenzaldehydeYield 93.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of [3-(benzyloxy)-4-fluorophenyl]methanol (14 mg) in DCM (0.7 mL) was added manganese dioxide (140 mg) at ambient temperature. After 22 hours, the reaction mixture was filtered through a bed of Celite and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=10:1) to give 3-(benzyloxy)-4-fluorobenzaldehyde (13 mg).

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. customevaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=10:1)

Sources & evidence

ORD record
ord-5dc314935a024a769c784718ca4e337b
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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