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

HRID 2304023Notes

Reaction equation

HRID 2304023 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>C1(C)C=CC=CC=1.[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 88%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (66.0 g) was dispersed in toluene (660 ml) and manganese dioxide (594 g, type HMH, manufactured by Toso) was added over 1 hr at 15-30° C. The mixture was stirred at 20-30° C. for 1 hr. The reaction mixture was filtered and washed with toluene (330 ml). The solvent was evaporated under reduced pressure to give nearly pure 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (57.6 g, 88%) as pale-yellow white crystals. Various spectrum data of the crystals were the same as those obtained in Example 18.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene (330 ml)
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7fee6095598b4235aaa4d91df86db8f4
Source dataset
uspto-grants-2002_08
Patent number
US06433196B1

Reaction notes

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