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The desired product, benzoic acid (3), is obtained by the following work-up: [2] Synthesis of benzoic acid with work-up step in red. The reaction mixture containing the Grignard reagent is allowed to warm to room temperature in a water bath to allow excess dry ice to evaporate. Any remaining Grignard reagent is quenched by the addition of water.
Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. [1] It is typically performed during the work-up step following a chemical synthesis to purify crude compounds [2] and results in the product being largely free of acidic or basic impurities.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C 6 Cl 2 (CN) 2 O 2. This oxidant is useful for the dehydrogenation of alcohols, [3] phenols, [4] and steroid ketones. [5] DDQ decomposes in water, but is stable in aqueous mineral acid. [6]
In another example, the Nicolaou's total synthesis of Taxol uses this reaction, although coupling stops with the formation of a cis-diol, rather than an olefin. Optimized procedures employ the dimethoxyethane complex of TiCl 3 in combination with the Zn(Cu). The first porphyrin isomer, porphycene, was synthesised by McMurry coupling. [8]
For example, nonylmagnesium bromide reacts with methyl p-chlorobenzoate to give p-nonylbenzoic acid, in the presence of Tris(acetylacetonato)iron(III) (Fe(acac) 3), after workup with NaOH to hydrolyze the ester, shown as follows. Without the Fe(acac) 3, the Grignard reagent would attack the ester group over the aryl halide. [21]
The mechanism of fluorination by DAST parallels that of sulfur tetrafluoride. Attack of the hydroxyl group of the substrate on sulfur and elimination of hydrogen fluoride lead to an alkoxyaminosulfur difluoride intermediate. Nucleophilic attack by fluoride, either by an S N 1 [5] or S N 2 [6] pathway, leads to the product. Although clean ...
Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. [11] Alternatively the workup may be via the Ing–Manske procedure , involving reaction with hydrazine . This method produces a precipitate of phthalhydrazide (C 6 H 4 (CO) 2 N 2 H 2 ) along with the primary amine:
The mechanism for the reduction of a nitrile to an aldehyde with DIBAL-H. The hydride reagent Diisobutylaluminium hydride, or DIBAL-H, is commonly used to convert nitriles to the aldehyde. [14] Regarding the proposed mechanism, DIBAL forms a Lewis acid-base adduct with the nitrile by formation of an N-Al bond. The hydride is then transferred to ...