Capstone – Ibuprofen GroupZach Bensley (Project Manager)

Kate Penrod (Literature Manager)DJ Hall (Equipment & Materials)Naomi Bryner (Safety Manager)

Structure SchemeO OH Cl MgCl

O

OH

NaBH4 HCl Mg 1. CO2

2. HCl

1-(4-isobutylphenyl)ethanone1-(4-isobutylphenyl)ethanol

1-(1-chloroethyl)-4-isobutylbenzene(1-(4-isobutylphenyl)ethyl)magnesium chloride2-(4-isobutylphenyl)propanoic acid (ibuprofen)

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 %

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 Yield1.003 g

Experimental Yield74.712 g – 73.270 g = 1.442 g

Percent Yield = -30.26%

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