Capstone – Ibuprofen Group

1. Capstone – Ibuprofen Group Zach Bensley (Project Manager) Kate Penrod (Literature Manager) DJ Hall (Equipment & Materials) Naomi Bryner (Safety Manager)

2. Structure Scheme 1-(4-isobutylphenyl)ethanone 1-(4-isobutylphenyl)ethanol 1-(1-chloroethyl)-4-isobutylbenzene (1-(4-isobutylphenyl)ethyl)magnesium chloride 2-(4-isobutylphenyl)propanoic acid (ibuprofen)

3. Reduction of p-isobutylacetophenone • In a sep funnel • P-isobutylacetophenone (2.00 mL) in MeOH (6 mL) • Sodium borohydride (0.50 g), reacted 10 min • Hydrochloric acid (3M, 20 mL), reacted 25 min • Extract with PET (3 x 10 mL) • Evaporate excess solvent • Percent yield: 47.48 %

4. Halogenation of 1-(4-isobutylphenyl)ethane • In a sep funnel • Small hydrochloric acid (12 M) to transfer 1-(4-isobutylphenyl)ethanol • Shake (2 min) • Extract with PET (3 x 10 mL) • Dry with Na2SO4 • Evaporate excess solvent • Percent yield: - 30.26 % Theoretical Yield 1.003 g Experimental Yield 74.712 g – 73.270 g = 1.442 g Percent Yield = -30.26%

5. Making the Grignard Intermediate • In an RBF • Oven dried Mg (1.0 g) with 1-(4-isobutylphenyl)ethane (0.50 mL), THF (20 mL)and 1,2-dibromoethane (6 drops) • Reflux with drying tube attached to top • Grignard formation seen when foaming (30 min) • Cool in a water bath • Does not indicate solvent evaporation