Dimethyl Sulfoxide → p-(Trifluoromethoxy)benzaldehyde

HRID 1590373Notes

Reaction equation

HRID 1590373 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:12])([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1371844-(Trifluoromethoxy)benzenemethanol

Product 1

HCID 69573p-(Trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol was oxidised using the conditions of Swern (oxalyl chloride, 2.05 ml; dimethyl sulphoxide, 3.33 ml and triethylamine, 14.8 ml) in dichloromethane to give 4-trifluoromethoxy benzaldehyde (4 g). NMR 1H: 10.04(2H,s), 7.98(2H,d), 7.35(2H,d).

Sources & evidence

ORD record
ord-7e4aa1523aac4f7abbd64f4b799305ea
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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