Transcript Capstone * Ibuprofen Group

Zach Bensley (Project Manager)
Kate Penrod (Literature Manager)
DJ Hall (Equipment & Materials)
Naomi Bryner (Safety Manager)
Capstone –
Ibuprofen
Group
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)
Reduction of pisobutylacetophenone
 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-(4isobutylphenyl)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)
Theoretical Yield
1 𝑚𝑜𝑙
196.721 𝑔
1.003 g × 178.266 𝑔 × 1 𝑚𝑜𝑙 = 1.107 𝑔
Dry with Na2SO4
 Evaporate
excess solvent
Experimental Yield
74.712 g – 73.270 g = 1.442 g
 Percent yield: - 30.26 %
Percent Yield
1.107 𝑔 −1.442 𝑔
× 100 % = -30.26%
1.107 𝑔
Making the Grignard
Intermediate
 In




an RBF
Oven dried Mg (1.0 g) with 1-(4isobutylphenyl)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