91060-96-7 → 2-Methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde

HRID 256392Notes

Reaction equation

HRID 256392 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]([CH3:11])[CH2:8][C:7]=2[CH:12]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]([CH3:11])[CH2:8][C:7]=2[CH:12]=1)=[O:1]

Participants

4

Reactant 1

HCID 2016367091060-96-7

Product 1

HCID 5956932-Methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 680 mg (4.14 mmole) 5-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 100 ml methylene dichloride was added 5.44 g manganese dioxide in one portion and the mixture stirred at room temperature overnight or until the reaction was complete as evidenced by thin-layer chromatography. The mixture was then filtered and the solvent evaporated to provide the title compound in quantitative yield. 1H-NMR(CDCl3)ppm(delta): 1.6 (d, 3H), 2.7-3.6 (m, 1H), 5.1 (m, 2H), 6.8 (d, 1H), 7.6 (m, 2H), 9.8 (s, 1H).

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-151e75c5eda54341bcf7c06aaa6445dc
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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