1-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalene

Abstract

In the title compound, C19H15ClO3, the dihedral angle between the naphthalene ring system and the benzene ring is 72.06 (7)°. The 4-chloro­phenyl group and the carbonyl group are almost coplanar. An inter­molecular C—H⋯O hydrogen bond is formed between an H atom of the 4-chloro­phenyl group and the O atom of one meth­oxy group, forming a zigzag chain along the a axis.

7-Methoxy-1-(4-nitrobenzoyl)naphthalen-2-yl 4-nitrobenzoate

“…For electrophilic aromatic substitution of naphthalene derivatives, see: . For the structures of closely related compounds, see: Muto et al (2010); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008); ; Mitsui et al (2009); Nagasawa et al (2010); Watanabe et al (2010). Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/ MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al, 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.…”

“…For example, (2-hydroxy-7-methoxynaphthalen-1-yl)(4-methylphenyl)methanone (Nagasawa et al, 2010) and (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone prepared by regioselective demethylation form intramolecular hydrogen bond between the carbonyl group and the adjacent hydroxy one. Besides, (4-chlorobenzoyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2009) has similar non-coplanar configuration to 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008). As a part of our continuous studies on the molecular structures of this kind of homologous molecules, the crystal structure of the title compound, 1-monoaroylated naphthalene bearing 4-nitrobenzoyloxy group at 2-position is discussed in this report.…”

(4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone

“…Recently, we reported the crystal structures of 1-aroylated 2,7-dimethoxynaphthalenes, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008), (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone , (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2009), 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (Mitsui, Nakaema, Nagasawa et al, 2010) and (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui, Nagasawa, Watanabe et al, 2010). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the structure of crystal of 2,5-dibromo-4-(4-chlorobenzoyl)-3-hydroxy-6-methoxynaphthalene, (I).…”

Chemospecific and Regioselective Ethereal Methyl-Oxygen Bond Cleavage Behavior of Aroylated Dimethoxynaphthalenes by Combined Action of AlCl<sub>3</sub> and Aroyl Group

“…In refluxing toluene solution, the two kinds of alkyl-oxygen bonds were thoroughly cleaved (Entry 10). Figure 1 displays the crystal structures of aroylated 2,7-dimethoxynaphthalenes (1aa and 7aa) [15,16] and aroylated 2-hydroxy-7-methoxynaphthalenes (2ba and 8ba) [17,18]. In 1-monoaroyl-2,7-dimethoxynaphthalene 1aa, the aroyl group non-coplanarly attaches to the naphthalene ring.…”