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Synthesis of Benzocaine lab report
Multistep synthesis
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A multistep synthesis procedure was used to synthesize benzocaine from p-toluidine (Scheme 1). In step one, p-toluidine was acetylated to produce p-acetotoluidide to protect the amine from oxidation. In step two, the methyl substituent on p-acetotoluidide was oxidized to produce p-acetamidobenzoic acid. In step three, p-acetamidobenzoic acid was hydrolyzed to remove the protecting group to produce p-aminobenzoic acid. In step four, p-aminobenzoic acid was esterified to produce benzocaine. A melting point range (Table 1) and 1H NMR spectrographs (Figures 1-4) were acquired for each product to confirm product identity at each step. The experimental melting range for each compound was within one to two degrees of the literature melting point which indicated possible contaminates. This was due to incomplete drying and/or errors during synthesis. 1H NMR spectra were acquired for each compound at 300 MHz and were provided by Dr. Kim White. The 1H NMR spectrum for each compound was analyzed below (Figures 1-4). The 1H NMR for p-acetotoluidide (Figure 1) contained five significant signals. Four of the signals were produced by p-acetotoluidide while the fifth signal (7.25 δ) was produced by the 1H NMR solvent, CDCl3. Due to proton exchange due to hydrogen bonding, there was no significant signal produced for the hydrogen bonded to the amide group. Due to this quality of hydrogen bonding the signal can manifest as broad, at the wrong chemical shift, or be absent. In this case, the signal produced by the hydrogen bonded to the amide group was absent. A list of the types of hydrogens and their chemical shifts for p-acetotoluidide was recorded (Table 2). The 1H NMR for p-acetamidobenzoic acid (Figure 2) contained five significant signa... ... middle of paper ... ...d, water (10 mL) was added and the resulting solution was neutralized to pH 7-8 by adding sodium carbonate (1.51 g, 14.2 mmol). The mixture was extracted twice with dichloromethane (two 10 mL portions). The combined organic layers were washed with water (10 mL) and sodium chloride (10 mL). The remaining organic layer was dried with anhydrous sodium sulfate. The solution was filtered and the remaining solvent was evaporated on a hot plate. Crystallization of benzocaine occurred. The crystals were recrystallized with methanol and water while heating. The reaction was cooled in an ice bath. The pale yellow precipitate was removed via vacuum filtration and dried under continuous filtration (0.17 g, 1.03 mmol). MP = 85-87 ͦC (literature value 88-90 ͦC); 1H NMR (300 MHz, CDCl3): δ 7.83-7.86 (d, 2H), 6.61-6.64 (d, 2H), 4.27-4.34 (q, 2H), 4.10 (s, 2H), 1.32-1.37 (t, 3H).
The percent yield of products that was calculated for this reaction was about 81.2%, fairly less pure than the previous product but still decently pure. A carbon NMR and H NMR were produced and used to identify the inequivalent carbons and hydrogens of the product. There were 9 constitutionally inequivalent carbons and potentially 4,5, or 6 constitutionally inequivalent hydrogens. On the H NMR there are 5 peaks, but at a closer inspection of the product, it seems there is only 4 constitutionally inequivalent hydrogens because of the symmetry held by the product and of this H’s. However, expansion of the peaks around the aromatic region on the NMR show 3 peaks, which was suppose to be only 2 peaks. In between the peaks is a peak from the solvent, xylene, that was used, which may account to for this discrepancy in the NMR. Furthermore, the product may have not been fully dissolved or was contaminated, leading to distortion (a splitting) of the peaks. The 2 peaks further down the spectrum were distinguished from two H’s, HF and HE, based off of shielding affects. The HF was closer to the O, so it experienced more of an up field shift than HE. On the C NMR, there are 9 constitutionally inequivalent carbons. A CNMR Peak Position for Typical Functional Group table was consulted to assign the carbons to their corresponding peaks. The carbonyl carbon, C1, is the farthest up field, while the carbons on the benzene ring are in the 120-140 ppm region. The sp3 hybridized carbon, C2 and C3, are the lowest on the spectrum. This reaction verifies the statement, ”Measurements have shown that while naphthalene and benzene both are considered especially stable due to their aromaticity, benzene is significantly more stable than naphthalene.” As seen in the reaction, the benzene ring is left untouched and only the naphthalene is involved in the reaction with maleic
The primary goal of this laboratory project was to identify an unknown compound and determine its chemical and physical properties. First the appearance, odor, solubility, and conductivity of the compound were observed and measured so that they could be compared to those of known compounds. Then the cation present in the compound was identified using the flame test. The identity of the anion present in the compound was deduced through a series of chemical tests (Cooper, 2009).
...e 3. Both letters A and B within the structure of trans-9-(2-phenylethenyl) anthracene, that make up the alkene, have a chemical shift between 5-6 ppm and both produce doublets because it has 1 adjacent hydrogen and according to the N + 1 rule that states the number of hydrogens in the adjacent carbon plus 1 provides the splitting pattern and the number of peaks in the split signal, which in this case is a doublet.1 Letters C and D that consist of the aromatic rings, both are multiplets, and have a chemical shift between 7-8 ppm. 1H NMR could be used to differentiate between cis and trans isomers of the product due to J-coupling. When this occurs, trans coupling will be between 11 and 19 Hz and cis coupling will be between 5 and 14 Hz, showing that cis has a slightly lowered coupling constant than trans, and therefore have their respective positions in a product. 2
Results: Through a melting point reading, it was determined that the product obtained was 2,4-Dibromoanisol mp 55-58 C. The products obtained by my partners, were determined to be: (p-bromoacetanilide mp 160-165 C) and (2,4,6 tribromoaniline, mp of 108-110 C) respectively.
Zhang X., Tang H., Ye C. and Liu M. (2006). Structure-based drug design: NMR-based approach for ligand-protein interactions. Drug Discovery Today: Technologies. 3 (3), pp. 241-245.
After performing the second TLC analysis (Figure 4), it was apparent that the product had purified because of the separation from the starting spot, unlike Figure 3. In addition, there was only spot that could be seen on the final TLC, indicating that only one isomer formed. Since (E,E) is the more stable isomer due to a less steric hindrance relative to the (E,Z) isomer, it can be inferred that (E,E) 1,4-Diphenyl-1,3-butadiene was the sole product. The proton NMR also confirmed that only (E,E) 1,4-Diphenyl-1,3-butadiene formed; based on literature values, the (E,E) isomer has peaks between 6.6-7.0 ppm for vinyl protons and 7.2-7.5 ppm for the phenyl protons. Likewise, the (E,Z) isomer has vinyl proton peaks at 6.2-6.5 ppm and 6.7-6.9 ppm in addition to the phenyl protons. The H NMR in Figure 5 shows multiplets only after 6.5 ppm, again confirming that only (E,E) 1,4-Diphenyl-1,3-butadiene formed. In addition, the coupling constant J of the (E,E) isomer is around 14-15 Hz, while for the (E,Z) isomer it is 11-12 Hz. Based on the NMR in Figure 5, the coupling constant is 15.15 Hz, complementing the production of (E,E)
The IR spectrum that was obtained of the white crystals showed several functional groups present in the molecule. The spectrum shows weak sharp peak at 2865 to 2964 cm-1, which is often associated with C-H, sp3 hybridised, stretching in the molecule, peaks in this region often represent a methyl group or CH2 groups. There are also peaks at 1369 cm-1, which is associated with CH3 stretching. There is also C=O stretching at 1767 cm-1, which is a strong peak due to the large dipole created via the large difference in electronegativity of the carbon and the oxygen atom. An anhydride C-O resonates between 1000 and 1300 cm-1 it is a at least two bands. The peak is present in the 13C NMR at 1269 and 1299 cm-1 it is of medium intensity.
Ensure gloves are worn at all times when handling strong acids and bases within the experiment of the preparation of benzocaine. 4-aminobenzoic acid (3.0g, 0.022 moles) was suspended into a dry round-bottomed flask (100cm3) followed by methylated sprits (20 cm3). Taking extra care the concentrated sulphuric acid of (3.0 cm3, 0.031 moles) was added. Immediately after the condenser was fitted on, and the components in the flask were swirled gently to mix components. It should be ensured that the reactants of the concentrated sulphuric acid and the 4-aminobenzoic acid were not clustered in the ground glass joint between the condenser itself and the flask. In order to heat the mixture to a boiling point, a heating mantle was used and then further left for gently refluxing for a constituent time of forty minutes. After the duration of the consistent forty minutes the rou...
yield of the pure product was determined to be 95.42%. PURPOSE The purpose of this lab was to perform an electro-philic aromatic substitution and determine the identity of the major product. TLC was used to detect unreacted starting material or isomeric products present in the reaction mixture. RESULTS The theoretical yield of the m-nitrobenzoate was determined to be 4.59 grams.
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
Mixed melting point was used to confirm the identity of the product. The smaller the range, the more pure the substance. When the two substances are mixed; the melting point should be the same melting range as the as the melting range obtained after filtering. If the mixed melting point is lower one taken from the crystals, then the two substances are different.
23. S. Alwarappan, S. Boyapalle, A. Kumar, C.-Z. Li and S. Mohapatra, J. Phys. Chem. C, 2012, 116, 6556–6559
6. Rouhi, A. M. (2003, July 28). C&EN: SCIENCE & TECHNOLOGY - Monosodium Glutamate. Retrieved March 17, 2014, from https://pubs.acs.org/cen/whatstuff/stuff/8130sci3.html
7- When describing the properties of JNJ 40279486, the authors highlight the selectivity of the compound over the hERG channel. Explain wh...
Plontke, R. (2003, March 13). Chemnitz UT. TU Chemnitz: - Technische Universität Chemnitz. Retrieved April 1, 2014, from http://www.tu-chemnitz.de/en/