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

HRID 1243916Notes

Reaction equation

HRID 1243916 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

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-bdedf521ba804a24b1346078551d8a36
Source dataset
uspto-grants-2006_10
Patent number
US07119215B2

Reaction notes

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