2,3-dihydro-1,4-benzodioxin-5-ylmethanol → 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

HRID 1174671Notes

Reaction equation

HRID 1174671 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][OH:12])[C:5]=2[O:4][CH2:3][CH2:2]1>C1COCC1.[O-2].[Mn+4].[O-2].O=[Mn]=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 27761822,3-dihydro-1,4-benzodioxin-5-ylmethanol2×

Product 1

HCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehydeYield 88%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2,3-dihydro-1,4-benzodioxin-5-ylmethanol (Intermediate A1) (commercially available from Aldrich) (3 g, 18.1 mmol) in THF (100 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (10 g, 115 mmol) at rt. The mixture was heated to 35° C. for 2 h and 60° C. for 4 h followed by 18 h at room temperature (rt). The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 20% EtOAc: hexanes to give 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) 2.6 g (88%).

Workup

  1. customat rt
  2. custom(rt)
  3. filtrationThe mixture was filtered through celite
  4. customthe solvent was removed under vacuum
  5. customThe residue was purified by chromatography on silica gel with 20% EtOAc

Sources & evidence

ORD record
ord-9be0b0b968f541abab89ed52802cf6f7
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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