1-propan-2-yl-2-propan-2-yloxybenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. prepared 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 The ether phase was washed with Claisen solution, water being added separation of phases The combined aqueous phases was extracted with ether the extract being added to the prior retained organic phase the combined material was dried over anhydrous magnesium sulfate Ether was removed by evaporation the residue was distilled

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 15 g of isopropyl (2-isopropylphenyl) ether was added 8 g of 1% fluorided alumina. The mixture was placed in a 300 cc stirred autoclave and the system was flushed with nitrogen and left under a nitrogen atmosphere. The autoclave was heated to 150° C. for 1 hour with stirring during which time the pressure reached 200 psig. The cooled reaction mixture was taken up in acetone, filtered, and the solvent was removed on a rotary evaporator. The residue was analyzed by gas-liquid phase chromatography (glpc) which showed the presence of 2-isopropylphenol (10%), isopropyl(2-isopropylphenyl) ether (28%), 2,6-diisopropylphenol (60%), and 2,4,6-triisopropylphenol (2%). Thus, the 2,6-diisopropylphenol was formed with 83% selectivity. the system was flushed with nitrogen left under a nitrogen atmosphere with stirring during which time the pressure The cooled reaction mixture filtered the solvent was removed on a rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The following description is representative of the rearrangement of an alkyl phenyl ether. A mixture of 15 g isopropyl (2-isopropylphenyl) ether and 5 g of catalyst (gamma-alumina, silica-modifed alumina, or aluminum phosphate) in a 300 ml stirred autoclave under nitrogen may be heated for 2-6 hours with stirring. After the reaction mixture has cooled to room temperature a solvent such as acetone may be added and the mixture filtered. Solvent may be removed by evaporation, under reduced pressure if desired, and the formed 2,6-diisopropylphenol may be isolated by fractional distillation. may be heated for 2-6 hours with stirring may be added the mixture filtered Solvent may be removed by evaporation, under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. prepared 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 The ether phase was washed with Claisen solution, water being added separation of phases The combined aqueous phases was extracted with ether the extract being added to the prior retained organic phase the combined material was dried over anhydrous magnesium sulfate Ether was removed by evaporation the residue was distilled

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 15 g of isopropyl (2-isopropylphenyl) ether was added 8 g of 1% fluorided alumina. The mixture was placed in a 300 cc stirred autoclave and the system was flushed with nitrogen and left under a nitrogen atmosphere. The autoclave was heated to 150° C. for 1 hour with stirring during which time the pressure reached 200 psig. The cooled reaction mixture was taken up in acetone, filtered, and the solvent was removed on a rotary evaporator. The residue was analyzed by gas-liquid phase chromatography (glpc) which showed the presence of 2-isopropylphenol (10%), isopropyl(2-isopropylphenyl) ether (28%), 2,6-diisopropylphenol (60%), and 2,4,6-triisopropylphenol (2%). Thus, the 2,6-diisopropylphenol was formed with 83% selectivity. the system was flushed with nitrogen left under a nitrogen atmosphere with stirring during which time the pressure The cooled reaction mixture filtered the solvent was removed on a rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The following description is representative of the rearrangement of an alkyl phenyl ether. A mixture of 15 g isopropyl (2-isopropylphenyl) ether and 5 g of catalyst (gamma-alumina, silica-modifed alumina, or aluminum phosphate) in a 300 ml stirred autoclave under nitrogen may be heated for 2-6 hours with stirring. After the reaction mixture has cooled to room temperature a solvent such as acetone may be added and the mixture filtered. Solvent may be removed by evaporation, under reduced pressure if desired, and the formed 2,6-diisopropylphenol may be isolated by fractional distillation. may be heated for 2-6 hours with stirring may be added the mixture filtered Solvent may be removed by evaporation, under reduced pressure