HWB
OH
1
2
Intermediate
3
Intermediate
H2SO4, H2O
Acetone
2
DCM, -78°C
then
Pyridine
0°C
Choose 3:
H3C(O)Cl
MeBr
AlCl3
FeBr3
Zn/Hg
H2SO4 +
CrO3
Na2Cr2O7
Aspirin/
Acetyl-
Salicylate
MgSO4, H2SO4
DCM, tBuOH, 0°C
Look at the following syntheses-
What types of transformations do you recognize?
What don't you recognize?
Do the bond disconnections make sense?
morpholine, S
then H2O+
Boots process
AcCl
AlCl3
NaOH
1. CH3OH, H2SO4
2. NaH, CH3I
2. resolution
(S)-naproxen 2
KOtBu
1. Ac2O
2. OH-, heat
NH2OH
2-naphthol
Boots-Hoechst-Celanese (BHC) process
1) Mg
2) H3C-CO2CO2-CH3, H3C
Br
(1)-naproxen
N-alkylglucamine
resolved as insoluble salt
Pope-Peachy method
(S)-naproxen, >95% ee
Raney-Ni
Ibuprofen 1
Make up 2 syntheses of phenacetin, HOWEVER...
a) start with ethoxybenzene and use nitration in one of your steps
b) start with phenol, use a Friedel-Crafts reaction (which one?!)
and you may want to use either oxidation or the
Schmidt Rearrangement as (a) key transformative step(s).