Prof Tessier

Synthesis of ibuprofen

There are two major syntheses used to prepare ibuprofen. The original synthesis was
by the Boots Co.(Fig. 1). A newer synthesis is by the BHC Co. (Fig. 2).








Figure 1.
Boots Co. synthesis of
ibuprofen (1960s)

Fragments of
molecules that are
circled are lost as
waste products.
Figure 1 was adapted from that in: Introduction to Green Chemistry: Instructional Activities for
Introductory Chemistry American Chemical Society: Washington, DC, 2002, p. 38.









Figure 2.
BHC Co. synthesis of
ibuprofen (1990s)

Fragments of
molecules that are
circled are lost as
waste products.
Figure 2 was adapted from that in: Introduction to Green Chemistry: Instructional Activities for
Introductory Chemistry American Chemical Society: Washington, DC, 2002, p. 39.

A big difference between the Boots and BHC syntheses of ibuprofen is the percent atom
economy which can be defined as
% atom

=
(#mols)(M desired product)
economy ((#mols)(M all products)
= the sum of
M = molecular or formula weight
#mols = coefficient in the balanced equation

Tables 1 and 2 give data for each of the two syntheses of ibuprofen that should allow you to
calculate the atom efficiency. Each reagent (starting material) is listed and its molecular weight
is given in the lefthand column. In the middle column, the formula and mass of the portion of
the reagent that ends up in the ibuprofen is listed. In the right-most column, the formula and
mass of the portion of the reagent that is wasted is listed. The bottommost line is a sum of the
lines above it. Under each table is a net equation for the multi-step process.
Ni (catal yst)
Table 1 Atom economy in the Boots synthesis of ibuprofen
Reagent Used in ibuprofen Unused in ibuprofen
Formula M
r
Formula M
r
Formula M
r

C
10
H
14
134 C
10
H
13
133 H 1
C
4
H
6
O
3
102 C
2
H
3
27 C
2
H
3
O
3
75
C
4
H
7
ClO
2
122.5 CH 13 C
3
H
6
ClO
2
109.5
C
2
H
5
ONa 68 0 C
2
H
5
ONa 68
H
3
O 19 0 H
3
O 19
NH
3
O 33 0 NH
3
O 33
H
4
O
2
36 HO
2
33 H
3
3
Total Ibuprofen Waste products
C
20
H
42
NO
10
ClNa 514.5 C
13
H
18
O
2
206 C
7
H
24
NO
8
ClNa 308.5
Net equation: C
20
H
42
NO
10
ClNa C
13
H
18
O
2
+ C
7
H
24
NO
8
ClNa


Table 2 Atom economy in the green synthesis of ibuprofen
Reagent Used in ibuprofen Unused in ibuprofen
Formula M
r
Formula M
r
Formula M
r

C
10
H
14
134 C
10
H
13
133 H 1
C
4
H
6
O
3
102 C
2
H
3
O 43 C
2
H
3
O
2
59
H
2
2 H
2
2 0
CO 28 CO 0 0
Total Ibuprofen Waste products
C
15
H
22
O
4
266 C
13
H
18
O
2
206 C
2
H
4
O
2
60
Net equation: C
15
H
22
O
4
C
13
H
18
O
2
+ C
2
H
4
O
2



Questions

1. Using the data from the last line in Table 1, calculate the percent atom economy of the Boots
synthesis of ibuprofen






2. Using the data from the last line in Table 2, calculate the percent atom economy of the Boots
synthesis of ibuprofen