Uses
Useful in the preparation of chalcones, flavonoids, and phenylephrine. It is an active component of castoreum, which is used as a tincture in some perfumes and as a food additive.
Synthesis
General procedure for the synthesis of 3-hydroxyacetophenone from 3-iodoacetophenone: 3-iodoacetophenone (1.0 mmol), CuCl? (13.4 mg, 0.1 mmol), KOH (336 mg, 6.0 mmol), ethylene glycol (12 μL, 0.2 mmol), and a solvent mixture of DMSO/H?O were sequentially added to the test tube fitted with a magnetic stirrer ( 1.0 mL/0.5 mL). The reaction mixture was placed in a preheated 120 °C oil bath under argon protection and stirred for 24 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was extracted by partitioning with 5% HCl aqueous solution and ethyl acetate. The organic phase was washed sequentially with water and saturated saline, dried over anhydrous MgSO? and concentrated under reduced pressure to remove the solvent. The crude product was further purified by column chromatography (eluent: EtOAc/hexane) to afford the target product 3-hydroxyacetophenone.
References
[1] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
[2] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 315 - 318
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 315 - 318
[5] Synlett, 2016, vol. 27, # 12, p. 1814 - 1819
