Dimethyl Sulfoxide → 2,3-Dihydro-2,2-dimethyl-4-benzofurancarboxaldehyde

HRID 342093Notes

Reaction equation

HRID 342093 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2=[C:7]([CH2:11][OH:12])[CH:8]=[CH:9][CH:10]=[C:4]2[O:3]1.CS(C)=O.C(Cl)(=O)C(Cl)=O>C(N(CC)CC)C>[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2=[C:7]([CH:11]=[O:12])[CH:8]=[CH:9][CH:10]=[C:4]2[O:3]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 18787456HCID 18787456, compound

Product 1

HCID 187874682,3-Dihydro-2,2-dimethyl-4-benzofurancarboxaldehydeYield 122.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2,2-Dimethyl-2,3-dihydro-benzofuran-4-methanol (7.35 g, 41 mmol) was oxidized using DMSO, oxalyl chloride, and triethyl amine similar to the above procedures to give the product as a clear oil (8.87 g, 100%).

Sources & evidence

ORD record
ord-349e233286a6440bade4f50d69e07253
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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