Dimethylformamide → 4,5-Dimethoxy-2-methylbenzaldehyde

Participants

Reaction Steps

Freshly distilled POCL3 (50.6 ml) was added dropwise during 30 min to a stirred mixture of 4 -methylveratrole (65.7 g) and DMF (30 g) freshly distilled after standing two days over CuSO4. Heating overnight on a steam bath under reflux gave a deep brown, viscous solution which when cooled was admixed with 600 ml water. Addition of excess 10% NaOH solution separated out a yellow oil which was extracted with benzene. The combined extracts were washed with water, dried, and evaporated to give a viscous yellow oil. Crystallization from alcohol gave 3.4 g of the aldehyde as a white powder, mp 74°-75°(Lit. 74°). Nmr (δ): 2.58 (s, 3H), 3.90 (s, 3H), 3.95 (s, 3H), 6.68 (s, 1H), 7.30 (s, 1H), 10.20 (s, 1H).

Provenance & Evidence