p-Toluenesulfonic acid → 1-Dimethoxymethyl-2-fluoro-4-trifluoromethyl-benzene

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1C=O.[CH:14](OC)([O:17][CH3:18])[O:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:16][O:15][CH:14]([O:17][CH3:18])[C:3]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[F:1]

Komponenten

Edukt 4

HCID 6101p-Toluenesulfonic acid

HCID 9005Trimethyl orthoformate

HCID 10340Sodium Carbonate

HCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 231124321-Dimethoxymethyl-2-fluoro-4-trifluoromethyl-benzeneAusbeute 98 %

Versuchsvorschrift

A solution of 2-fluoro-4-trifluoromethylbenzaldehyde (10.0 g, 52.0 mmol), trimethyl orthoformate (55.0 g, 520 mmol) and a catalytic amount of p-toluene sulfonic acid (5 mol %) was stirred at room temperature for 24 hours. The resulting solution was saturated with the addition of solid Na2CO3 and stirred for 15 minutes. The mixture was then filtered and the solution was evaporated. The residue was diluted with ether and evaporated yielding 12.1 g (98%) of the desired product as an oil.