Diethyl Ether → 4,4'-Dimethylbenzhydrol

Participants

Reaction Steps

With reference to FIG. 1, the preferred alcohol is synthesized via a Grignard reaction. First, the magnesium salt of 4-bromotoluene, the Grignard reagent, is prepared in an anhydrous non-nucleophilic ether-based solvent. Examples of suitable solvents include, but are not limited to, diethyl ether, diisopropylether, dioxane and tetrahydrofuran. The preferred solvent is tetrahydrofuran. After preparation of the Grignard reagent, para-tolualdehyde was added to the room temperature solution of the magnesium salt at a rate sufficient to create a reflux. A sufficient time was allowed for the addition of the Grignard reagent to the aldehyde derivative, then the reaction was quenched with a proton source. Following work up of the reaction mixture, 4,4'-dimethylbenzhydrol is isolated (compound I).

Provenance & Evidence