Water → Dibenzyl

Participants

Reaction Steps

To 10 g of 6-methylveratraldehyde under a nitrogen atmosphere in 75 ml dry THF was added dropwise 1.5 equivalents benzylmagnesium chloride in 20 ml dry THF. After stirring overnight at room temperature, 20 ml water was added. The residue remaining after most of the THF had been distilled off was added to an additional 100 ml water and extracted with ether to give a yellow oil. Distillation under reduced pressure gave bibenzyl resulting from coupling of the Grignard reagent and a quantitative yield of the adduct 12 as a colorless viscous oil, bp 170°-175°(0.05 mm Hg). Nmr (δ): 2.08 (s, 3H), 2.88 (distorted doublet, J - 6 cps, integration for 3 H suggests coincidence with the alcohol proton), 3.75 (s, 6H), 4.96 (t, J = 6 cps, 1H), 6.52 (s, 1H), 7.00 (s, 1H), 7.15 (s, 5H),. Anal. Calcd. for C17H 20 O3 : C, 74.97; H, 7.40. Found: C, 75.38; H, 7.43.

Provenance & Evidence