[3-(Benzyloxy)-4-methylphenyl]methanol → 3-(Benzyloxy)-4-methylbenzaldehyde

HRID 881596Notes

Reaction equation

HRID 881596 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[CH3:15])[CH:16]=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 24721056[3-(Benzyloxy)-4-methylphenyl]methanol

Product 1

HCID 161013893-(Benzyloxy)-4-methylbenzaldehydeYield 39.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-benzyloxy-4-methylphenyl)methanol (1.0 g) in dichloromethane (50 mL) was added manganese dioxide (2.5 g), and this mixture was stirred at room temperature for 2 days. The insoluble material was removed by filtration and this filtrate was concentrated under reduced pressure. This residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.39 g)

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure
  3. customThis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6f0715ca5d994056bedf93c762e7f939
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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