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: %

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: %
Theoretical Yield
1.003 g × 1 𝑚𝑜𝑙 𝑔 × 𝑔 1 𝑚𝑜𝑙 =1.107 𝑔
Experimental Yield
g – g = g
Percent Yield
1.107 𝑔 −1.442 𝑔 𝑔 ×100 % = %

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