Crystal Structure of (4-Benzoyl-2-methyl-phenoxy)-acetic acid ethyl ester

Abstract

Analogues of phenoxy acetic acid are known to be important compounds, and have been widely investigated for pharmaceutical uses. 1 The efficiency of phenoxy acetic acid analogues as chemotherapeutic agents, especially as inhibitors of human, rabbit and rat platelet aggregation 2 and analgesic properties, which are comparable to that of morphine, is well documented. In addition to this they exhibit nootropic 3 and antiinflammatory activity, which is related to ibuprofen. 4 Besides, considerable work has been carried out with regard to both the synthesis and pharmacological activity of benzophenone derivatives. The most important applications of benzophenones are as anti-inflammatory property, 5 anti-cancer, 6 anti-fungal 7 and anti-malarial 8 agents. With retrospect to the above observations, this presentation is directed towards the facile synthesis and Xray crystallographic study of (4-benzoyl-2-methyl-phenoxy)-acetic acid ethyl ester.(4-Benzoyl-2-methyl-phenoxy)-acetic acid ethyl ester was obtained by refluxing a mixture of 4-hydroxyl-2-methyl benzophenone (2.94 g, 0.013 mol) and ethyl chloroacetate (3.18 g, 0.026 mol) in dry acetone (50 ml) and anhydrous potassium carbonate (2.69 g, 0.019 mol) for 8 h. The reaction mixture was cooled, and the solvent was removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 ¥ 50 ml). The ether layer was washed with a 10% sodium hydroxide solution (3 ¥ 50 ml), followed by water (3 ¥ 30 ml), and then dried over anhydrous sodium sulphate and evaporated to dryness to obtain X-ray Structure Analysis Online The structure of the title compound, (4-benzoyl-2-methyl-phenoxy)-acetic acid ethyl ester (C18H18O4), was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the orthorhombic space group Pbca with the following unit-cell parameters: a = 36.993(2), b = 10.1567 (7), c = 8.3441(6)Å, Z = 8. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected and refined by full-matrix least-squares procedures to a final R-value of 0.0690 for 2155 observed reflections. The dihedral angle between the benzoyl ring and the methyl substituted phenyl ring is 59.4(1)˚. The crystal structure is stabilized by C-H·O and C-H·p hydrogen bonds that link the molecules into infinite chains.

Design, Synthesis, and Anticancer Properties of Novel Benzophenone‐Conjugated Coumarin Analogs

“…The ether layer was washed with 10% sodium hydroxide solution (3 × 50 mL) followed by water (3 × 30 mL) and then dried over anhydrous sodium sulfate and evaporated to dryness to obtain crude solid, which, on recrystallization with ethanol, afforded compounds 5a – n . Compound 5a is taken as a representative example to explain characterization data .…”

Synthesis, Xanthine Oxidase Inhibition, and Antioxidant Screening of Benzophenone Tagged Thiazolidinone Analogs

“…The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 × 50 mL). The ether layer was washed with 10% sodium hydroxide solution (3 × 50 mL) followed by water (3 × 30 mL) and then dried over anhydrous sodium sulfate and evaporated to dryness to obtain crude solid, which on recrystallization with ethanol afforded compounds 5a and 5b .…”