5-Fluoro-2-(hydroxymethyl)benzoic acid → 5-Fluoro-2-formylbenzoic acid

HRID 2361287Notes

Reaction equation

HRID 2361287 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][OH:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>O1CCCC1.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 468313515-Fluoro-2-(hydroxymethyl)benzoic acid

Product 1

HCID 451570385-Fluoro-2-formylbenzoic acidYield 41.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-fluoro-2-(hydroxymethyl)benzoic acid (0.518 g, 3.04 mmol) and manganese(IV) oxide (3.71 g, 42.6 mmol) in tetrahydrofuran (25 mL) was stirred at room temperature for 16 hr. The insoluble material was removed by filtration through CELITE®. The filtrate was concentrated under vacuum to dryness. The residue was dissolved in CH2Cl2 (100 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.211 g, 1.255 mmol, 41.2% yield) as a white solid.

Workup

  1. customThe insoluble material was removed by filtration through CELITE®
  2. concentrationThe filtrate was concentrated under vacuum to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-73088f2ae7fb4ad3b9414e44c0a9ef94
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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