N-Acylation and O-Acylation

Britany Dyer (Guzman)

November 1,, 2017

Aim: To synteisze acetaminophen using p-Aminophenol and acetic anhydride. Additionally to synthesize
acetyly salicylic acid with the use of acetic anhydride, salicylic acid, and phosphoric acid

Chemicals Equipment
Name Structure Physical Test Tube Filtrating flask Hirsch
P- , °C, funnel
aminopehnol HO NH2 g/mol

Acetic H3C , °C,

anhydride O g/mol
O
Hot Plate Beaker Sand
O
Bath
H3C
Salyicyclic CH3 Solid, 5 6 5 6
4 7 4 7

3 8 3 8

Acid °C,
2 9 2 9
1 10
1 1 10

OH
g/mol
OH

Reagents: Water, Posphoric Acid (H3PO4)

Setup: Procedure:
A literature1 procedure was followed without any
modifications

5 6 5 6
4 7 4 7

3 8 3 8

2 9 2 9
1 10
1 1 10

Chemical Reaction:
Synthesis of Acetominophenon
H3C
O H3C
HO NH
HO NH2 + O
+ H2O
CH3 + O
O HO
O
H3C
Sythesis of Acetyly Saicycli Acid
CH3 H3C CH3
O H3C
OH
OH + O + H3PO4
+ O
O HO
OH O
H3C
H3C O