User:CorrelationSpec/Work-Up Sandbox

In chemistry, work-up refers to the series of manipulations required to isolate and purify the product(s) of a chemical reaction.^[1] Typically, these manipulations may include:

deactivating any unreacted reagents by quenching a reaction.
cooling the reaction mixture or adding an antisolvent to induce precipitation, and collecting or removing the solids by filtration, decantation, or centrifugation.
changing the protonation state of the products or impurities by adding an acid or base
removal of solvents by evaporation.
separating the reaction mixture into organic and aqueous layers by liquid-liquid extraction.
purification by chromatography, distillation or recrystallization

Workup steps are not always included in reaction schemes

Examples

Isolation of Benzoic Acid

The Grignard reaction between phenylmagnesium bromide and carbon dioxide in the form of dry ice gives the conjugate base of benzoic acid. The desired product, benzoic acid, is obtained by the following work-up:^[2]

Synthetic route of benzoic acid with workup 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
Dilute hydrochloric acid is added to the reaction mixture to protonate the benzoate salts, as well as to dissolve the magnesium salts. White solids of impure benzoic acid are obtained.
The benzoic acid is decanted to remove the aqueous solution of impurities, more water is added, and the mixture is brought to a boil with more water added to give a homogeneous solution.
The solution is allowed to cool slowly to room temperature, then in an ice bath to recrystallize benzoic acid.
The recrystallized benzoic acid crystals are collected on a Buchner funnel and are allowed to air-dry to give pure benzoic acid.

Dehydration of 4-methylcyclohexanol

Tert-butyl Ester Hydrolysis

In the hydrolysis of a tert-butyl ester, the starting material is treated with trifluoracetic acid. If the product is not volatile relative to the TFA

Once the reaction is complete, a simple workup can be completed by

Liquid-Liquid Extraction

References

^ Stevenson, Angus; Lindberg, Christine A., eds. (2010). "Workup". New Oxford American Dictionary (3rd ed.). Oxford University Press. ISBN 9780199891535.
^ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 0-534-40833-8.

[1] Stevenson, Angus; Lindberg, Christine A., eds. (2010). "Workup". New Oxford American Dictionary (3rd ed.). Oxford University Press. ISBN 9780199891535.

[2] Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 0-534-40833-8.

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