Experiment 4

Flow Chart
Overall balanced reaction

Reagent table
Reagent Acetaminophen NaOH in EtOH 1-Iodobutane 4-
(1.0M) Butoxyacetanilid
e

Molar Mass 151.16 gmol-1 40.00 gmol-1 184.02 gmol-1 207.27 gmol-1

Density - - 1.62 gmL-1 -

Experiment 1.00g 8.27 mL 1.32 mL 1.37g

Quantity

Amount in moles 0.00662 0.00827 0.0116 0.00662

Equivalents 1.00 1.25 1.75 1.00

Equipements
- Two tablets of tylenol (500mg per tablet) - magnetic stir bar
- Weighing paper - NaOH
- Motar - sand
- Reflux condenser - clamps
- Heating plate - single channel pipette
- TLC - capillary tubes
- Hirsch funnel

Procedure
Setting up the Acetaminophen Alkylation Reaction
1) Grind 2 tablets of extra strength Tylenol (500 mg of acetaminophen per tablet)
using a mortar
2) Use a folded weighing paper to transfer the powder to a round bottom flask with
a magnetic stir bar.
3) Add the calculated volume of 1.0 M NaOH in EtOH solution.

Heating to Reflux
1) Set up reflux condenser
2) Place the reaction mixture into a heating insert as per the demo set-up at the
front of the lab. Use sand to fill in the gaps between the round bottom flask and
the insert.
3) Begin stirring such that the reaction mixture stirs well (approx. 300 RPM).
 4) Fit the flask with a reflux condenser, turn on the water and gently heat the
reaction until reflux is achieved. When heating to reflux using the heat-on insert,
a good rule of thumb is to set the hotplate about 20 °C higher than the boiling
point of the solvent. Once reflux has started, continue to heat the reaction for 10
minutes. (~98.4°C)
5) Add the calculated amount of 1-iodobutane to the hot solution through the top of
the reflux condenser using a single channel pipette
6) Remove condenser flask

Monitoring the Alkylation Reaction by TLC

1) Use 3:1 ethyl acetate:hexane mixture as mobile phase
2) Take a sample of the reaction mixture by lifting the condenser
3) Insert a clean capillary tube in the opening of the round bottom flask
4) Spot in the RM and CS lanes
5) Reconnect the joints of the condenser and round bottom flask
6) Place standard limiting solution on the SM and CS lanes
7) Place into TLC chamber
8) While TLC is running, stop the reaction by adding an additional 4 mL of the 1.0M
NaOH solution through the top of reflux condenser and continue to reflux for an
additional 5 minutes

Isolation of 4-Butoxyacetanilide
1) Remove round bottom flask from heating mantle
2) Filter the reaction mixture using a hirsch funnel
3) Place approx 30 ml of ice water into the funnel to wet the filter paper
4) Filtrate and the insoluble fillers remain in the Hirsch funnel
5) Isolate 4-butoxyacetanilide by suction filtration
6) Measure mass and melting point
Mechanism

Data to collect