4'-Hydroxy-3'-methylacetophenone

Chemical Properties

white to light beige crystalline powder or

Uses

4''-Hydroxy-3''-methylacetophenone is used in the synthesis of 3-De(hydroxymethyl)-3-methyl Salmeterol (D230650), which is an impurity of β2-Adrenergic agonist Salmeterol (S090100).

Preparation

Preparation by dealkylation of 4-hydroxy-5-methyl-2-iso-propylacetophenone with aluminium chloride in chloro-benzene at 50° (53%).

Definition

ChEBI: 4-hydroxy-3-methylacetophenone is a monohydroxyacetophenone that is acetophenone carrying methyl and hydroxy groups at positions 3 and 4, respectively. It has a role as a volatile oil component and an insect attractant. It is a monohydroxyacetophenone, a member of phenols and a hydroxytoluene. It is functionally related to an acetophenone.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 23, p. 738, 1980 DOI: 10.1021/jm00181a008