Microscale – KMnO4 oxidation of alkylbenzenes

Objective To obtain benzoic acid by oxidation of alkyl functional groups from aromatic compounds using potasium permanganate (KMnO4). Background The alkyl chains attached to aromatic rings are likely to be oxidized to acid if they have at least one hydrogen at the benzyl position. Permanganate is an oxidizing agent widely used both in organic and … Read more

Microscale – Preparation of 9-bromoanthracene

Objective To acquaint students with the free-radical halogenation reactions, in particular a bromination using N-bromosuccinimide (NBS). Background N-bromosuccinimide (NBS) is used as a highly specific bromination agent both in free-radical substitutions and in electrophilic additions of unsaturated systems, because releases small quantities of bromine. Anthracene can be brominated at position 9 by a radical process. … Read more

Microscale – Compounds for the fragrance industry (ester synthesis)

Objective To prepare various esters at a microscale with applications in the fragrance industry by combining different carboxylic acids and alcohols that are selected because they are common in Organic Chemistry laboratory experiments. Background Esters are compunds with the following general formula R-C(=O)O-R’ formula. They result from by a reaction between a carboxylic acid and … Read more

Synthesis of racemic 1,1′-bi-2-naphthol

Objective Synthesis of racemic 1,1′-bi-2-naphthol by an oxidative coupling reaction in aqueous media. Background 1,1′-Bi-2-naphthol is a compound that can be used as a ligand for transition- metal. 1,1′-Bi-2-naphthol is an example of molecule that presents atropisomers. Enantiomeric pure complex of such derivatives can be used as a catalyst in some asymmetric syntheses but may … Read more

Preparation of 1-butyl-3-methylimidazolium derivative

Objective To synthesize in water 1-butyl-3-methylimidazolium derivative, which has the property of being a ionic liquid. Background The so-called ionic liquids are salts in which at least one of their components is an organic compound that has a delocalized charge. This characteristic prevents the formation of stable crystal lattices because both the cation and the anion are … Read more

Obtaining phthalates from recycled polymers (PET)

Objective Recycled polyethylene terephthalate (PET) by a depolymerization reaction and use of the product for the synthesis of a diester of high added value. Background A large number of synthetic polymers are materials that are usually obtained from monomers originating from the petrochemical industry.   Once the lifetimecycle of objects made from polymers has expired, … Read more

Synthesis of tetrahydropyrimidinone (Biginelli reaction)

Objective To perform one-pot synthesis of a tetrahydropyrimidinone by a three-component reaction (Biginelli reaction). Background The Biginelli reaction, first described in 1893, is a three-component reaction between an aldehyde, a β-ketoester, and urea to yield in a one-pot procedure dihydropyrimidones. This reaction is a quick and easy method to synthesize heterocycles, compounds with a great … Read more

Microscale – Synthesis of 2-iodobenzoic acid (Sandmeyer reaction)

Objective To produce at microscale iodobenzoic acid by the formation of an intermediate diazonium salt (Sandmeyer reaction). Background The Sandmeyer reaction is a versatile synthetic tool by which an amino group on an aromatic ring is replaced with a wide range of substituents by converting an amino group attached to an aromatic ring into a … Read more

Microscale – Preparation of 4-methyl-3- and 4-methyl-2-nitroacetanilide from 4-methylaniline

Objective To prepare and isolate two isomers in the nitration reaction of 4-methylaniline using two synthetic strategies. Background In electrophilic aromatic substitution reactions, the amino groups have a strong activating character directing ortho and para. However, when the amino group is protonated due to the positive charge on the nitrogen atom, it is strongly deactivating … Read more