2-Bromopropane → Isopropyl 2-isopropylphenyl ether

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Reaction Steps

A solution of 2-isopropylphenol (75 g, 0.54 mol) in 60 ml methanol was added, under nitrogen, to a solution of sodium methoxide, prepared by reacting 13.1 g (0.57 mol) sodium with 150 ml dry methanol. To this stirred solution was added isopropyl bromide (82.2 g, 0.66 mol) dropwise over several hours, after which the reaction mixture was heated at reflux overnight. The cooled mixture was filtered to remove solids and methanol was removed on a rotary evaporator. The residue, containing both liquid and solid, was treated with about equal volumes of diethyl ether and water, with the aqueous phase then separated and discarded. The ether phase was washed with Claisen solution, water being added to facilitate separation of phases, and the organic phase retained. The combined aqueous phases was extracted with ether, the extract being added to the prior retained organic phase, and the combined material was dried over anhydrous magnesium sulfate. Ether was removed by evaporation and the residue was distilled to afford isopropyl (2-isopropylphenyl) ether.

Provenance & Evidence