6-(Hydroxymethyl)-2-benzofuran-1(3H)-one → 3-Oxo-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 1766872Notes

Reaction equation

HRID 1766872 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][C:9]2=[O:12])=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4]>[O:12]=[C:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([CH:2]=[O:1])[CH:11]=2)[CH2:7][O:8]1

Participants

3

Reactant 1

HCID 178625846-(Hydroxymethyl)-2-benzofuran-1(3H)-one

Product 1

HCID 178625183-Oxo-1,3-dihydroisobenzofuran-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

According to a similar procedure to that described in Example 4-(3), 6-(hydroxymethyl)-1 (3H)-isobenzofuranone (3.25 g, 20.8 mmol) obtained from Example 1-(4) or Example 1-(6) and activated manganese dioxide (33 g) were reacted, and the reaction mixture was worked up to afford the title compound as a crude solid. The crude solid was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate) to afford the title compound (2.45 g, 76% yield) as a solid (mp. 134° C.)

Sources & evidence

ORD record
ord-196154be239149329c8429d8995dd198
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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