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November 12, 2011 Dear Ms.

Quinn, A sample of 4-phenylphenol was synthesized through a Suzuki coupling reaction, using a series of aryl halides. First, the crude product was synthesized through the use of two separate aryl halides: 4-iodophenol (0.20 mmol, 0.044 g) and 4-bromophenol (0.20 mmol, 0.034g) treated with phenylboronoic acid (0.20 mmol, 0.024 g) and potassium carbonate (0.60 mmol, 0.82 g). 10% Pd/C by mass (used as a catalyst) and 2.0 mL of water, was then added to the mixture before it was set to reflux for about forty minutes. After cooled to room temperature, the mixture was filtered to separate the catalyst, and then recrystallized using a 50:50 methanol/water mixture to form the product. The recrystallized products were then tested for their melting points in order to determine the purity of the compound. During the above process, the Pd/C catalyst was recovered quite easily indicating that it is a good catalyst to use if trying to be cost conscious. The obtained crystal product was a powdery solid with a grayish color. The product obtained from 4-bromophenol gave a better yield (21.75%) than the 4-iodophenol (17.9%). When a melting point analysis was conducted, the product from 4bromophenol had a closer range (165-166.6C) to the predicted melting point of phenylphenol (167C) than 4-iodophenol did (161.8-163.2C) indicating that it is more pure, and yields more product. A cost/ yield analysis was conducted to determine the most cost effect method for producing the 4-substituted-biphenyl compound. It was determined that the moles of phenylphenol produced per dollar spend for 4-bromophenol ($382/mol) was marginally higher than it was for 4-iodophenol ($359/mol), but because the 4bromophenol obtains a better yield of the product it is the optimum choice for large scale synthesis of 4-phenylphenol.

Table I. Reagents Compoun d Phenylboro nic acid Potassium Carbonate 4iodophenol 4bromophen ol Water Methanol Hydrochlori c Acid Calculations I. Structure Molecular Weight (g/mol) 121 138 220 173 18.02 64.70 Boiling Point (C) N/A N/A 138 235-236 100 64.7 Melting Point (C) 216-219 891 89.0-94.0 64.0-68.0 0 -98.0 Amount Used 0.024g 0.082g 0.044g 0.034g N/A N/A N/A Moles Used 1.98E-4 5.94E-4 2.00E-4 1.96E-4 N/A N/A N/A

C6H7BO2 K2CO3 C6H5IO C6H5BrO H 2O CH3OH HCl

Table II. Product Compound 4phenylphenol Structure C12H10O Molecular Weight (g) 170 Melting Point (C) 167 Boiling Point (C) 305-308

Calculations II. Product from 4-iodophenol:

Product from 4-bromophenol:

Percent Yield Calculations Using 4-bromophenol

Using 4-iodophenol

Table III. Melting Point Ranges Compound Produced From 4-iodophenol 4-bromophenol Observations: Upon first mixing, the solution began as a black liquid most likely due to the color of the Palladium catalyst. A top layer formed after fifteen minutes of refluxing After about thirty minutes of refluxing, the solution began to have a tar like appearance very viscous. When the HCl was added, the solution bubbled as it reacted. Predicted Melting Point Range (C) 167 167 Experimental Melting Point Range (C) 161.8-163.2 165-166.6

Table IV. - Cost Analysis Compound Molecular Weight (g/mol) Cost ($/g) Cost ($/mol) Phenylphen ol (mmol) Yield/Cost (mol/$)

4chlorophenol 4bromophenol 4-iodophenol

129 173 220

0.261 2.21 1.63

36.3 83.1 64.42

0 0.0435 0.0359

0 382 359

Calculations III. For 4-Chlorophenol:

For 4-Bromophenol:

For 4-Iodophenol: