3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

Participants

Reaction Steps

To a 1 molar solution of 3-hydroxybenzaldehyde (10 g, 0.819 moles) in isopropyl alcohol (820 mL) was added 2-iodopropane (146.2 g, 0.860 moles) followed by powdered potassium carbonate (339.5 g, 0.457 moles) and the mixture was heated to reflux under nitrogen for a minimum of 8 hrs. The reaction was complete by TLC. Water was added to the cooled reaction until all salts were dissolved. The mixture was extracted with ether three times. The combined ether extracts were washed with water, 2 M NaOH and again with water until clear (three times) then brine. The organic layer was dried over magnesium sulfate and filtered and evaporated to give the desired product as a pale oil.

Provenance & Evidence