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DISCUSSION

To synthesis flavone, it is required 3 steps of reaction which the first are preparation of 2-
benzoyloxyacetaphenone from 2-hydroxyacetaphenone, which can be prepared or
commercially available. In this stage, 2-benzoyloxyacetaphenone was produced by
benzoylation of the phenolic OH group with benzoyl chloride in pyridine by heating in the
existence of potassium hydroxide. Based in the result above, number of mol for 2-
hydroxyacetaphenone and benzoyl chloride are 0.019833 and 0.03002 mol respectively.
Considering the 2-hydroxyacetaphenone have the small number of mol than benzoyl chloride,
thus 2- hydroxyacetaphenone is the limiting reactant. From the calculation, the percentage yield
for 2-benzoyloxyacetaphenone is 42.13%. The percentage yield is low due the value of actual
yield is low than theoretical yield. This may be caused by the incomplete or competing
reactions and loss of sample during recovery.

In the next stage, 2-benzoyloxyacetaphenone will undergoes the Baker-Venkataraman


rearrangement to produce ortho-hydroxydibenzoylmethane. However, in this step, our group
was not be able to obtain the product. The yellow precipitate of the potassium salt is not seen
in this step, it is no precipitate at all. This may because of the lack of reactivity of the 2-
hydroxyacetaphenone which attributed to the resonance effect of the methoxy groups
deactivating the ketone to enolate the formation. This affect the next stage of this experiment.

In final stage, we proceed with the product we obtained above which involve crystallization of
the ortho-hydroxydibenzoylmethane to flavone in the presence of acetic acid and sulfuric acids,
after that the product we obtained was not colourless needles that expected to be flavone.

The first stage is important because it may cause failed to other steps if the first stage goes
wrong. Like in our experiment. Also, other factors like human error, systematic error can
contribute to the failed of experiment.

Based on the Jain et al (1982) research published, they come out with the related process that
may be able to overcome the error in the first stage. They found that, when the 2-
hydroxyacetophenone starting materials, containing either methoxy or methyl groups at
various positions, were subjected to reaction with an aroyl chloride and either aqueous
potassium carbonate or potassium hydroxide solution, in benzene, under phase-transfer-
catalysis conditions (n-tetrabutylammonium hydrogen sulfate), the reaction resulted in the
formation of the corresponding dibenzoylmethanes in near quantitative yields. The benzene
solution, upon treatment with p-toluenesulfonic acid, then afforded cyclized flavones in
excellent yield. With their newly developed condition, other researcher were able to use this
modified Baker-Venkataraman rearrangement to synthesize a variety of hydroxyflavone too.
This modified method also can be used to overcome this error in future.

Since our group does not obtain any product, we share the NMR results from other groups.
This is too show how the NMR result should be obtained. NMR is used to confirm the purity f
the product. Based on the NMR spectrum , 10 protons was observed similar with flavone that
have 10 protons. The deshielded proton should be proton d, due to the resonance effects and
also due to the electronegativity of oxygen near the proton.

CONCLUSION

The synthesis of flavone from 2-hydroxyacetaphenone was failed. The objectives is not
achived.

References

Ameen, D., & Snape, T. J. (2015). Mechanism and application of Baker–Venkataraman O→


C acyl migration reactions. Synthesis, 47(02), 141-158.

Jain, P. K., Makrandi, J. K., & Grover, S. K. (1982). A facile Baker-Venkataraman synthesis
of flavones using phase transfer catalysis. Synthesis, 1982(03), 221-222.