1,4-Di-t-butyl-2,5-dimethoxybenzene Introduction: A Friedel-Crafts alkylation reaction will be performed using an activated substrate, 1,4-dimethoxybenzene, and a readily formed carbocation,

t-butyl alcohol in the presence of sulfuric acid, as the electrophile. A mixture of 1,4-dimethoxybenzene and t-butyl alcohol will be kept in an ice bath, and the sulfuric acid will be added dropwise using a separatory funnel so the temperature can be carefully controlled. A process of filtration and recrystallization will be carried out to collect the solid crystalline product. ****Reaction Data and Calculations: Temperatures (did it rise about 20?) Temperature reached during boiling Product produced Experimental: To a 250 mL Erlenmeyer flask, 6 g of 1,4-dimethoxybenzene, 10 mL of t-butyl alcohol, and 30 mL of acetic acid were added. The flask was warmed to dissolve. The mixture was cooled by placing the flask in an ice-water bath and swirled frequently. To a 50 mL Erlenmeyer flask, 30 mL of concentrated sulfuric acid was added and placed in an ice-water bath to cool. The mixture in the 125 mL flask were cooled to 0-5 degrees Celsius. The chilled H2SO4 was added to a 125 mL separatory funnel and placed above the 250 Erlenmeyer flask that contained the mixture. The sulfuric acid was added dropwise to the flask, and the flask was constantly swirled. The temperature of the reaction flask was kept between the 15-20 degree range during the addition. All of the acid was added and the reaction flask was continuously swirled while the temperature was maintained at 20-25 degrees for 5 minutes. The reaction mixture was cooled in an ice-water bath and ice and water were added to the reaction flask to the 200 mL mark. The product was cooled and collected on a large Buchner funnel. The solid was washed with cold water. (I think was skipped methanol paragraph double check!!!!) The reaction product was placed in a clean 125 mL Erlenmeyer flask and ___ mL dichloromethane was added. Anhydrous MgSO4 was added to the flask until the drying agent no longer clumped together. The flask was allowed to sit for 10 minutes and the dichloromethane solution was gravity filtered into a clean 125 mL Erlenmeyer flask. A boiling chip and 35 mL of methanol were added to the solution and heated to 60-62 degrees Celsius. The flask was allowed to stand for

crystallization to occur and the mixture was cooled in an ice-water bath. The solid product was collected by suction filtration and washed with ice-cold methanol. Results and Conclusions: The product produced from the Friedel-Crafts alkylation, 1,4-t-butyl-2,5dimethoxybenzene was a white crystalline substance.