Trimethyl orthoformate

Trimethyl orthoformate is an organic compound with the formula HC(OCH3)3. It is a colorless liquid that is used primarily as a reagent in organic synthesis. Trimethyl orthoformate is an ester of orthoformic acid and methanol. Due to its reactivity and versatility, it finds applications in a variety of chemical reactions, including trans-esterifications, and as a protecting group for aldehydes.

Properties

Trimethyl orthoformate is characterized by its boiling point of 103-105 °C and a density of 0.967 g/cm3. It is soluble in organic solvents but has limited solubility in water. The compound is stable under normal conditions but can react violently with strong oxidizing agents.

Synthesis

Trimethyl orthoformate can be synthesized through the reaction of methanol with chloroform and an alkali metal hydroxide, typically sodium hydroxide. This process involves the formation of orthoformic acid, which is then esterified with methanol to produce trimethyl orthoformate.

Applications

Organic Synthesis

In organic synthesis, trimethyl orthoformate is used as a reagent for the introduction of a formyl group into molecules. It serves as a convenient source of formaldehyde in the formylation of amines and can also be used to protect aldehydes and ketones as their dimethyl acetals or ketals, making it a valuable tool in the synthesis of complex organic molecules.

Protecting Group

Trimethyl orthoformate is often used as a protecting group for aldehydes during synthetic procedures. By converting aldehydes into their corresponding trimethyl orthoformate derivatives, it prevents unwanted reactions at the aldehyde functionality, allowing for further transformations of other functional groups within the molecule.

Safety

Trimethyl orthoformate is flammable and should be handled with care. It can cause irritation to the skin, eyes, and respiratory system upon exposure. Appropriate safety measures, including the use of personal protective equipment (PPE), should be taken when working with this chemical.

See Also

• Organic synthesis
• Protecting group
• Formylation
• Esterification