2,5-Bis(2-methoxyphenyl)furan

Xiang-Gao Meng, An-Xin Wu
2005 Acta Crystallographica Section E  
H 16 O 3 , the dihedral angles between the two benzene rings and the furan ring are 3.7 (1) and 1.0 (1) . C-HÁ Á Á andinteractions are observed in the crystal structure. Comment We have synthesized 2,5-bis(2-methoxyphenyl)furan, (I), according to the literature method of Wu et al. (1997) and its structure is reported here. The molecule is essentially planar (Fig. 1 ). Selected bond lengths and angles are listed in Table 1 . C-HÁ Á Á andinteractions are observed in the crystal structure (see
more » ... e 2 and Fig. 2 ). Analysis using PLATON (Spek, 2003) shows that the distance between the centroids of the C2-C7 and C12 i -C17 i benzene rings is 3.89 (1) A ˚[symmetry code: (i) x, 1 + y, z]. Experimental 3-Ethoxy-1-(2-methoxyphenyl)propan-1-one was first synthesized according to the literature (Pelter et al., 1982) . Sodium hydride (0.4 g, 80%) was washed with dry pentane and then suspended in dry CH 2 Cl 2 (10 ml). To this was added a solution of ethyl 3-(2methoxyphenyl)-3-oxopropanoate (2.2 g, 10 mmol) in dry CH 2 Cl 2 (15 ml) and then a solution of ethyl 2-bromo-3-(2-methoxyphenyl)-3oxopropanoate (3 g, 10 mmol) in dry CH 2 Cl 2 was added. The product was then refluxed with stirring for 3 h. The suspension was cooled, washed with water (20 ml), and dried (Na 2 SO 4 ). After removal of the solvent, the residue was purified, affording diethyl 2,3-bis(2methoxybenzoyl)succinate. Toluene-p-sulfonic acid (5 g) was added to a solution of diethyl 2,3-bis(2-methoxybenzoyl)succinate (2.2 g, 5 mmol) in dry benzene (50 ml). The mixture was refluxed for 8 h and concentrated. The residue was chromatographed on silica gel (light petroleum-ethyl acetate, 8:1 (v/v) to give diethyl 2,5-bis(2-methoxyphenyl)furan-3,4-dicarboxylate which was hydrogenated, oxidized and decarboxylated to give the title compound. Crystals suitable for X-ray analysis were obtained by recrystallization of the the title compound from ethanol over a period of two weeks.
doi:10.1107/s1600536805027911 fatcat:3zdr5cxizraczotvrnkqaaoovi