Hydrolysis of Methyl Salicylate
+ 2NaOH
+ H
2
O+ CH
3
OH
H
2
SO
4
The procedure in the book will be followed except,
mp will be determined during lab after some drying;
lab reports will be collected at the end of the period as usual
.
Procedure:
Reaction- Reflux
Use 250ml round bottom flask, and water condenser.
Dissolve 10g of NaOH in 50ml of water in a 250 ml erlenmeyer flask, then cool. ** Solution will heat up rapidly **
Transfer the basic solution and the 5.0g of Methyl Salicylate into the 250ml RBF.
Add Boiling Chips
Reflux for 30-40 minutes.
Crystallization
Transfer the reaction mixture to a 250 ml beaker once it has cooled to room temp.
Add 10 ml portions of 1M Sulfuric Acid until the reaction mixture is slightly acidic. Then add 15ml of additional 1M sulfuric acid.
Cool to O
o
C in ice bath
Collect by Vacuum Filtration.
Recrystallization
Transfer crude product to a 250ml erlenmeyer flask, and boiling chips and 100ml of water and bring to a boil.
If insoluble material is present use hot gravity filtration to remove impurities.
Cool and then place in ice bath
Collect by Vacuum Filtration.
Determine Final Mass and Melting Point
Allow the crystals to dry for at least 15 minutes on the aspirator.
+ 2NaOH 
+
H2O+ CH3OH
H2SO4