3'-Hydroxypropiophenone

The Uses of 3'-Hydroxypropiophenone

1-?(3-?Hydroxyphenyl)?-?1-?propanone is a reactant used to synthesize tricyclic fused pyridines, a family of alkaloids with antimalarial activity.

Preparation

Preparation by diazotization of m-aminopropiophenone, followed by decomposition of the diazonium salt obtained, (71%)
Also obtained by saponification of 3-acetoxypropiophenone (b.p.2 127–128°) with refluxing 10% sodium hydroxide for 2–3 h (83%)
Also obtained by reductive deamination of 2-amino-5-hydroxypropiophenone (diazotization, followed by decomposition of the diazonium salt formed with copper powder in ethanol)
Also obtained by reaction of ethylmagnesium bromide with 3-hydroxy-N, N-diethylbenzamide in refluxing n-butyl ether for 4 h (75%)
Also obtained by treatment of 3-methoxypropiophenone (b.p.0.05 70–76°) with pyridinium chloride at 210° for 30 min (85%)
Also obtained by treatment of 1-hydroxy-1-(3-hydroxyphenyl)propane (m.p. 105–107°) with DDQ in dioxane for 72 h (97%).