Scheme-9 Lab Report

Beta-nitroisosafrole is a less used precursor, but there is a large literature on the synthesis and reduction of nitro alkenes. This synthetic route isn't as popular due to the easier availability of precursors for MDP-2-P, and it also results in MDA which must then be further processed to give MDMA or any other N-alkyl homolog of MDA. There are numerous ways to convert beta-nitroisosafrole to MDA: LiAlH4, AlH3, electrolytic, Na(Hg), BH3 - THF / NaBH4, Raney Ni catalyst, Pd / BaSO4 catalyst, Zn (Hg). Beta-nitroisosafrole, when used, is commonly synthesized from piperonal. Beta-nitroisosafrole can also be used as a precursor for MDP-2-P, but this is not commonly done.

1. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene.

This experiment will involve the conversion of Benzoin into Benzil through oxidation using nitric acid. Benzoin was synthesized in a previous experiment using two Benzaldehyde molecules and thiamine hydrochloride as a catalyst. The reaction is known as a Benzoin condensation reaction. This experiment utilized a wide a variety of techniques including reflux; filtering using a Buchner funnel; a melting point analysis; and an IR spectroscopy. The total yield for Benzoin was 3.506 grams which resulted in a percentage yield of 74.74%. Melting point analysis showed that the literature melting point is 134-135 ᵒC, whereas the experiment melting point was 131-133 ᵒC. In the synthesis of Benzil, 2.328 grams of crude Benzil were obtained. Thus,

The 1-alkyl-3-acylindoles and the inverse regioisomeric 1-acyl-3-alkylindoles can be prepared directly from a common set of precursor materials and using similar synthetic strategies. The EI mass spectra for these isomers show a number of unique ions which allow for the differentiation of the 1-alkyl-3-acylindole compounds from the inverse regioisomeric 1-acyl-3-alkylindoles. The base peak at m/z 214 in the 1-n-pentyl-3-benzoylindole represents the M-77 cation fragment resulting from the loss of the phenyl group and this ion is not observed in the inverse isomer. The 1-benzoyl-3-n-pentylindole inverse regioisomer shows a base peak at m/z 105 for the benzoyl cation. Thus, these two base peaks are the result of fragmentation initiated at the carbonyl-oxygen for both isomers. The 1-pentyl-3-benzoylindole is characterized by the strong intensity carbonyl band at 1703 cm-1 while the amide carbonyl appears as a strong band of equal intensity at 1681 cm-1 in the 1-benzoyl-3-pentyl regioisomer.

Abstract: This procedure demonstrates the nitration of methyl benzoate to prepare methyl m-nitrobenzoate. Methyl benzoate was treated with concentrated Nitric and Sulfuric acid to yield methyl m-nitrobenzoate. The product was then isolated and recrystallized using methanol. This reaction is an example of an electrophilic aromatic substitution reaction, in which the nitro group replaces a proton of the aromatic ring. Following recrystallization, melting point and infrared were used to identify and characterize the product of the reaction.

Silver nitrate AgNO3 (≥99.0%) and PVP (Average molecular weight ~55,000) were purchased from Sigma-Aldrich. Ethylene glycol (EG) and Hydrochloric acid (HCl) were purchased from Merck specialities Pvt Ltd. All the chemicals were used as received without any purification. We synthesized silver nanocubes (Ag NCs) by a typical polyol method. In a typical synthesis, 12.5 mL of ethylene glycol was poured in 50 mL of round bottom flask and heated at 140°C for 1 h under stirring. An amount of 2.5 mL of HCl solution (3.3mM in EG) was quickly injected into the reaction mixture. After 10 min, 7.5 mL of AgNO3 solution (94mM in EG) and 7.5 mL of PVP (147mM in EG) solutions were simultaneously injected into the stirring solution. The reaction mixture was

The resulting mixture was magnetically stirred at 50 °C for 15 min. The reaction progress was monitored by TLC (n-hexane : EtOAc, 1 : 1). Upon the completion of the reaction, hot ethanol was added to the reaction mixture and the heterogeneous catalyst was simply separated by centrifugation. Next, the separated catalyst was washed with ethanol (3 × 15 mL) to be ready for utilizing in the next run. Then, the filtrate was evaporated and the resulting crude product was recrystallized from ethanol to afford the pure 4a product (0.39 g,

The Friedel-Crafts acylation reaction is an important and valuable electrophilic aromatic substitution reaction. First introduced in 1912 by Charles Friedel and James M. Crafts, this reaction allows large multi-step reactions to take place, and creates numerous types of products.1 Today, Friedel-Crafts reactions are among the most used electrophilic aromatic substitution reactions. In the electrophilic aromatic substitution class of reactions, functional groups are substituted onto an aromatic ring.2 Products such as ketones, hydrocarbons and phenols, phenol ethers, and keto acids can be produced by electrophilic aromatic substitution.1 These products can then undergo other reactions, allowing for the creation of many types of products. The products acquired can be used for a range of purposes, such as pharmaceuticals, pesticides, dyes, etcetera.3

(1) Advantages include some cost effective alternatives for catalysts used. The catalytic activity of the catalysts used did not decrease after multiple uses. This reaction is a good industrialization prospect. All reagents are commercially available.

Synthesis of 2,6-Dimethylaniline via Reduction of 2,6-Dimethylnitrobenzene 1) Weigh 1.0g of 2,6-dimethylnitrobenzene to dissolve in 10 mL of glacial acetic acid in a 50mL Erlenmeyer flask. 2) 4.6 grams of SnCl2•2H2O was dissolved in 8mL of concentrated HCl in a 25 mL flask. This procedure was performed inside a fume hood. 3) One portion of SnCl2 solution added into the nitroxylene solution, swirl and mix by magnetically, and let the mixture stand for 15 minutes. 4)

Using various alcohols, the substitution reactions (Sn2 and Sn) were utilized by helping with which functional groups reacted, in which way. Developing a mechanism for the alcohols are discussed.

This experiment produced a very high yield reaction, 80%. Again, the product was isolated using silica gel column chromatography using the wet method. Peaks on IR spectra match peaks found in literature. Although we were unable to completely remove catalyst, in several samples, the presence of the catalyst was diminished greatly.

Recently, Park et al. published an elaborated review on the use of zeolites, mesoporous catalysts and metal oxide catalysts for catalytic vapor cracking. Zeolites, due to their acidity and shape selective catalysis, are reported to be the most effective catalysts for the production of deoxygenated liquid fuel consisting of gasoline range aromatic hydrocarbons. The product composition of the upgraded bio-oils varied with Si/Al ratio and the pore structure of the zeolites. Low organic product yields and rapid deactivation of the catalysts are the drawbacks associated with zeolite catalysis. Recently, Carlson et al. demonstrated that high catalyst to feed ratios and high heating rates attenuate the catalyst deactivation despite improving organic product yields. Poor organic product yields (due to secondary cracking reactions) and the deactivation of HZSM-5 catalysts can be attributed to their high Brönsted acidity.

Chiral 1,3-diols 20 & 21 were obtained from the yeast-reduction products of 2-oxocyclopentane-and 2-oxocyclohexane carboxylates and excess MeLi, BuLi or PhLi. These ligands form titanium complexes 22 with TiCl(i-Pr0)3 which are effective catalysts for enantioselective nucleophilic addition of MeMgCl to benzaldehyde and 1-naphthaldehyde yielding 1-phenyl ethanol and 1-naphthyl ethanol respectively in good enantioselectivities.

5, 10, 15, 20-tetraphenylporphyrinatocobalt(II) showed good catalytic activity towards oxidation of 3,5-di-tert-butylcatechol to 3,5-di-tert-butyl-benzoquinone by dioxygen in dimethylformamide. The oxidation reaction was followed by measuring dioxygen uptake. The rate constant of oxidation reaction showed a linear dependence on catalyst concentration and saturation kinetics in both 3,5-di-tert-butylcatechol concentration and dioxygen pressure. The kinetic parameters have been determined using Michaelis-Menten approach. A mechanism has been suggested for the oxidation reaction.