Experiment #1

FRIEDEL-CRAFTS ACYLATION: SYNTHESIS OF 4-METHOXYACETOPHENONE

Chemistry-21225-08

The University of Texas Rio Grande Valley

Fall 2018

Dr. Srivastava

Magdaleno Calvo

20303916
Purpose: The purpose of this experiment was to synthesize 4-methoxyacetophenone by the method of
Fridel-Crafts acylation of anisole with acetic anhydride.

Introduction: The reactions made in this experiment are of the electrophilic aromatic substitution type.
These processes are characterized by the initial reaction of an electrophile, in this case Acylium Ion
(created by the loss of the acetate anion to the Lewis acid - AlCl3 -). with the pi bonds of a aromatic ring,
in this case Anisole, destroying the aromaticity and generating an intermediate resonance-stabilized
carbocation called cyclohexadienyl. Finally, the loss of a hydrogen ion from the cyclohexadienyl
intermediate reforms pi bond, generating acetic acid and reforming the Lewis acid catalyst: AlCl3.

Concepts:

Activating substituents: They make the aromatic ring more reactive by releasing electrons. Ortho- and
para-positions. Atom bonded to aromatic ring will carry - charge.

Deactivating substituents: It makes the aromatic ring less reactive, by withdrawing electrons.

Ortho- and para- positions. Atom bonded to aromatic ring will carry + charge

Procedure: The first step of the procedure of this experiment was to collect all the necessary materials.
Later the apparatus was assembled. Next, dichloromethane, anisole, and aluminum chloride (7ml, .55g,
and 1.45g) were mixed in a round-bottom flask - 25ml, dropwise of Acetic Anhydride was added, and the
reaction was heated for 10 minutes in the hot plate. . Then the 25mL bottom to the 5g ice bath was
passed, while the reaction was washed with 1 ml of sodium hydroxide and sodium chloride.
Subsequently, the mixture was transferred to a separatory funnel where the mixture was still rinsed
with sodium hydroxide and sodium chloride. After the reaction was dried with .5g of MgSO4. Then, the
layers were separated and the organic layer was placed in an Erlenmeyer flask where it was heated to
try to evaporate the remaining dichloromethane. Finally, the remaining residue in the Erlenmeyer flask
was plugged and stored for future use.
Conclusion: The objective of the experiment was to synthesize 4-methoxyacetophenone by using an
Electrophilic Aromatic Substitution, from which the expected results were not obtained. Most likely, the
amount of product obtained is less than the calculated. Some of the reasons why the experiment was
not so good, may be the agglutination of product that was observed during the transition from the
mixture to the separatory funnel due to the bad synchronization at the time of adding the milliliters of
3M NaOH, and NaCl.