Uses
2',3'-DIHYDROXYACETOPHENONE is a reagent used in the synthesis of antiproliferative agents, opioid receptor agonists, and anticoagulants.
Preparation
Also obtained by bioconversion of acetophenone through the living cells of Escherichia coli carrying plasmid pUC6256B expressing todCI-bphA2A3A4 and bphB (39.2%).
Definition
ChEBI: 2',3'-Dihydroxyacetophenone is an aromatic ketone.
Synthesis
The general procedure for the synthesis of 2,3-dihydroxyacetophenone from 2,3-dimethoxyacetophenone was carried out as follows: to 1M dichloromethane (68 ml) was added 1M boron tribromide solution at -70°C, followed by a solution of dichloromethane (100 ml) of 2,3-dimethoxyacetophenone (4.85 g, 26.9 mmol). The reaction mixture was cooled and stirred at room temperature for 2.5 hours. After completion of the reaction, methanol (70 ml) was added and stirring was continued for 1 hour. Subsequently, the reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (250 ml) and washed once with 2% NaHCO3 solution (30 ml), the organic phase was dried and the solvent was evaporated to give the crude product. The crude product was purified by methanol crystallization to give 3.10 g of the target compound as a yellow solid in 76% yield.1H NMR (300 MHz, CDCl3) δ ppm: 2.61 (s, 3H); 6.77-7.05 (t, 1H); 7.02 (dd, 1H); 7.36 (dd, 1H).
References
[1] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 183 - 192
[2] Patent: US5990142, 1999, A
[3] Chemische Berichte, 1913, vol. 46, p. 4019
[4] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10371 - 10387
