Ethyl Bromide → 3-Ethoxy-4-methoxybenzaldehyde

Participants

Reaction Steps

To a solution of 100 g of 3-hydroxy-4-methoxybenzaldehyde in 200 ml ethanol was added to solution of 44 g KOH in 44 ml H2O. The mixture dissolved upon heating to reflux and 56 ml ethyl bromide was then added slowly. A yellow solid began to precipitate after 15 min and heating of the mixture at reflux was continued overnight. Excess ethyl bromide and solvent were removed in vacuo and the residue was distributed between water and CHCl3. The CHCl3 layer was dried and evaporated to give a pale yellow oil which crystallized from ethanol to give 112 g (93%) of 3-ethoxy-4-methoxybenzaldehyde, mp 49.5°-50.5°(Lit.12 mp 50° -51°).

Provenance & Evidence