Mechanism + Description
Simple SN2 displacement of alcohol.
Many activated esters e.g. trifluoroethyl, benzoyl, trifluoroacetate etc can be hydrolysed with water or water-solvent mixtures alone or added to an organic solvent if needed for solubility. This should always be tried as a first line of investigation.
J.Am.Chem.Soc., 1958, 80, 2985 - Hydrolysis of t-Alkyl Trifluoroacetates
Relevant scale up example
Atom efficiency (by-products Mwt)
High – produces product and corresponding alcohol, negligible waste and water can be used as the solvent.
- Safety Concerns
None prominent. Higher temperatures may be required to push reaction to completion (stability of SM/product).
- Toxicity and environmental/aquatic impact
- Cost, availability & sustainable feedstocks
Cheap and readily available.
- Sustainable implications
Sustainable. Aqueous waste can potentially be directly bio-treated.