1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol → 1-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 2304022Notes

Reaction equation

HRID 2304022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1>COC(C)(C)C.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 99211661-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

Product 1

HCID 102204271-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
20 °C

Procedure

1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (299.3 g) and manganese dioxide (2.25 kg, type HMH, manufactured by Toso) were dispersed in t-butyl methyl ether (3.4 L) and the mixture was stirred at 10-30° C. for 6 hr. The reaction mixture was filtered and washed with t-butyl methyl ether (0.9 L). The solvent was evaporated under reduced pressure to give nearly pure 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (258.2 g, 87%) as pale-yellow white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with t-butyl methyl ether (0.9 L)
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-48ed420bdada47ee94d8929ed1d22fc3
Source dataset
uspto-grants-2002_08
Patent number
US06433196B1

Reaction notes

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