4-Hydroxyphenylacetone

4-Hydroxyphenylacetone (also known as p-Hydroxyphenylacetone, 4-HPPA, or 4-Hydroxybenzyl methyl ketone) is a chemical compound with the molecular formula C9H10O2. It is a derivative of phenylacetone, with a hydroxy group (-OH) attached to the phenyl ring at the para position.

Structure and Properties

4-Hydroxyphenylacetone is a white to light yellow crystalline solid at room temperature. It has a melting point of 71-74°C and a boiling point of 295°C. The compound is soluble in water and most organic solvents.

The structure of 4-Hydroxyphenylacetone consists of a phenyl group attached to an acetone moiety through a single carbon-carbon bond. The phenyl group has a hydroxy group attached at the para position, which is opposite to the carbon attached to the acetone.

Synthesis

4-Hydroxyphenylacetone can be synthesized through the Friedel-Crafts acylation of phenol with acetyl chloride in the presence of an acid catalyst such as aluminum chloride. The resulting product is then hydrolyzed to yield 4-Hydroxyphenylacetone.

Applications

4-Hydroxyphenylacetone is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of perfumes and flavors due to its pleasant, sweet aroma.

Safety and Precautions

As with all chemicals, 4-Hydroxyphenylacetone should be handled with care. It can cause irritation to the skin and eyes, and prolonged exposure can lead to more serious health effects. Always use appropriate personal protective equipment when handling this compound.

See Also

• Phenylacetone
• Friedel-Crafts Acylation
• Phenol

References

• The Merck Index, 14th Edition, Merck & Co., Inc., Whitehouse Station, NJ, USA, 2006.
• CRC Handbook of Chemistry and Physics, 89th Edition, CRC Press, Boca Raton, FL, USA, 2008.