Conversion of 2,4-dihydroxybenzaldehyde to 2-benzoyloxy-4-hydroxybenzaldehyde and structural characterization of both precursor and product

被引:7
|
作者
Hu, ZY
Hardie, MJ
Burckel, P
Pinkerton, AA [1 ]
Erhardt, PW
机构
[1] Univ Toledo, Ctr Drug Design & Dev, Toledo, OH 43066 USA
[2] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
关键词
2-benzoyloxy-4-hydroxybenzaldehyde; 2,4-dihydroxybenzaldehyde; hydrogen bonding; x-ray structure;
D O I
10.1023/A:1009570027191
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
2,4-Dihydroxybenzaldehyde can be acylated at the 2 position if the more reactive 4 position is first protected as the methylmethoxy ether. Deprotection permits isolation of 2-benzoyloxy-4-hydroxybenzaldehyde. 2,4-Dihydroxybenzaldehyde, C7H6O3, crystallizes in P2(1)/c, with a = 7.3762(6), b = 11.7455(9), c = 7.3149(6) Angstrom, beta = 90.533(2)degrees, Z = 4, and D-X = 1.448 g cm(-3). The individual molecules are characterized by an intramolecular hydrogen bond. The molecules form sheets with additional intermolecular hydrogen bonds. 2-Benzoyloxy-4-hydroxybenzaldehyde, C14H10O2, crystallizes in Pca2(1), with a = 24.2629(14), b = 3.8445(2), c = 12.3727(8) Angstrom, Z = 4, and D-X = 1.394 g cm(-3). The molecules consist of two planar halves twisted by 51.63(5)degrees about the ester linkage. Intermolecular hydrogen bonding joins the molecules into ribbons approximately parallel to c.
引用
收藏
页码:185 / 191
页数:7
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