4-Hydroxyphenylacetone

4-Hydroxyphenylacetone

Structural formula of 4-Hydroxyphenylacetone

4-Hydroxyphenylacetone is an organic compound with the chemical formula C₉H₁₀O₂. It is a phenolic ketone and a derivative of phenylacetone. This compound is of interest in the field of organic chemistry due to its role as an intermediate in the synthesis of various pharmaceuticals and its occurrence in certain metabolic pathways.

Chemical Structure and Properties

4-Hydroxyphenylacetone consists of a phenyl ring substituted with a hydroxy group at the para position and an acetone moiety. The presence of the hydroxy group makes it a phenolic compound, which can participate in hydrogen bonding, affecting its solubility and reactivity.

Physical Properties

- Molecular Weight: 150.18 g/mol - Appearance: White to off-white crystalline solid - Solubility: Soluble in organic solvents such as ethanol and ether

Chemical Properties

4-Hydroxyphenylacetone can undergo typical reactions of phenols, such as electrophilic aromatic substitution and oxidation. The ketone group can participate in reactions like nucleophilic addition and reduction.

Synthesis

4-Hydroxyphenylacetone can be synthesized through several methods, including the Friedel-Crafts acylation of phenol with chloroacetone, followed by hydrolysis. Another method involves the oxidation of 4-hydroxyphenyl-2-propanol.

Biological Role

In biological systems, 4-Hydroxyphenylacetone is a metabolite of certain catecholamines, such as dopamine. It is formed through the action of monoamine oxidase and other enzymes involved in the degradation of neurotransmitters.

Applications

4-Hydroxyphenylacetone is used as an intermediate in the synthesis of various pharmaceuticals, including antidepressants and antipsychotics. Its ability to undergo further chemical transformations makes it a valuable compound in medicinal chemistry.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 4-Hydroxyphenylacetone. It should be stored in a cool, dry place, and contact with skin and eyes should be avoided.

Related Pages

• Phenylacetone
• Phenol
• Ketone
• Organic chemistry