[5-(Benzyloxy)-3-methyl-1-benzofuran-2-yl]methanol → 5-(Benzyloxy)-3-methyl-1-benzofuran-2-carbaldehyde

HRID 2091350Notes

Reaction equation

HRID 2091350 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][OH:18])=[C:14]([CH3:19])[C:13]=2[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[C:14]([CH3:19])[C:13]=2[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66778297[5-(Benzyloxy)-3-methyl-1-benzofuran-2-yl]methanol

Product 1

HCID 866627535-(Benzyloxy)-3-methyl-1-benzofuran-2-carbaldehydeYield 96.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution (30 mL) of [5-(benzyloxy)-3-methyl-1-benzofuran-2-yl]methanol (2.8 g) synthesized in the above-mentioned (2) in toluene was added manganese dioxide (5 g), and the mixture was heated under reflux with a Dean-Stark trap for 1 hr. The reaction mixture was allowed to cool to room temperature, catalyst was filtered through celite. The filtrate was concentrated under reduced pressure to give the title object compound (2.68 g, 94%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux with a Dean-Stark trap for 1 hr
  3. filtrationcatalyst was filtered through celite
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-db20419ce3e349ce9c6ad723b9299081
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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