Preparation of p-cymene from limonene

Objective Synthesis of a bulk chemical (p-cymene) from a renewable feedstock (limonene). Background D-Limonene is the major constituent of citrus peel oils (90–95 %). Some 50,000 tons of limonene are produced annually by the citrus industry, this being an available renewable feedstock that can be used as the starting material for preparing several products and … Read more

Synthesis of chiral ethyl 3-hydroxybutanoate

Objective To performe a stereoselective reduction of a carbonyl compound with a biological reagent to obtain chiral ethyl 3-hydroxybutanoate. Background The reduction of ethyl acetoacetate using common baker’s yeast is an example of enzymatic reduction of carbonyl compounds to alcohols in the presence of ester groups. The procedure performed in water shows the stereoselective power … Read more

Synthesis of γ-tert-butyl-ε-caprolactone from oxidation of 4-tert-butylcyclohexanone

Objective To synthesize a bulk chemical (γ-tert-butyl-ε-caprolactone) from a renewable feedstock (4-tert-butylcyclohexanone) by oxidation reaction. Background The Baeyer-Villiger oxidation is a rearrangement transformation of ketones to give esters. This is a suitable and efficient method to synthesize lactones from cyclic ketones in a one-step reaction. In this experiment, 4-tert-butylcyclohexanone is transformed into γ-tert-butyl-ε-caprolactone using m-chloroperoxybenzoic … Read more

Preparation of benzyl butyl ether

Objective To perform ether synthesis using phase-transfer catalyst in a water-basic solution. Background In the usual Williamson ether synthesis, a primary alkyl halide reacts with an alkoside. The reaction conditions must be rigorous, paying special attention to the anhydrous solvent. Even a trace of water can spoil the reaction. However, the Williamson ether synthesis may … Read more

Preparation of dibenzylamine hydrochloride

Objective To perform a reductive amination in the solid phase. Background Reductive amination is the conversion of an aldehyde or a ketone into an amine via an intermediate imine. This reaction is considered the most remarkable way to synthesize complex amines, and a majority of amines prepared in the pharmaceutical industry are made by this … Read more

Microscale – Paal-Knorr synthesis of 2,5-dimethyl-1-phenylpyrrole

Objective To synthesize at microscale a heterocyclic compound, in particular, 2,5-dimethyl-1-phenylpyrrole using the Paal-Knorr synthesis. Background Among different types of cyclization reactions for preparing nitrogen heterocycles, one of the most popular methods for the synthesis of substituted pyrroles is known as the Paal-Knorr synthesis. In this experiment, a 1,4-dicarbonyl compound is heated with a primary … Read more

Microscale – Vanillin transformations

Objective To apply microscale procedures to the synthesis of three vanillin derivatives by means of functional group transformations. Background Vanillin (3-methoxy-4-hydroxybenzaldehyde) is a white crystalline compound that can be isolated from vanilla plant (Vanilla planifola), the highest concentration of this compound being in the seeds. It is one of most commonly used flavorings and perfuming … Read more

Microscale – Wintergreen oil from aspirin tablets

Objective To prepare the high valued-added methyl salicylate from commercial aspirin tablets by two simultaneous transesterification-esterification reactions. Background Methyl salicylate is an ester salicylic acid derivative found in many plants. Wintergreen Gaultheria procumbens is one of the species with the highest concentration of this compound, and therefore this molecule is known as Gaultheria essential oil. … Read more

Microscale – Synthesis of anthrone from anthraquinone

Objective To produce anthrone at microscale by reduction of one of the anthracene carbonyl groups. Background Anthrone is a tricyclic aromatic ketone that can be used, for example for calorimetric determinations of carbohydrates in biological fluids. It can be synthesized by partial reduction of anthraquinone with several reagents, as sodium hydrogen sulfite NaHSO3, tin chloride … Read more

Microscale – Partial hydrogenation of a vegetable oil with cyclohexene and Pd(C) (margarine production)

Objective To perform a non-conventional hydrogenation of a vegetable oil (olive, palm, sunflower seed, etc.) to produce margarine. Background Margarine has traditionally been manufactured by hydrogenation of vegetable oils (olive, palm, sunflower seed, etc.) by an industrial process for converting these oils into a solid, stable, and spreadable substance. The procedure followed in this experiment … Read more