2-(4-Chloro­phen­yl)-2-oxoethyl 4-hy­droxy­benzoate

Hoong-Kun Fun; Tara Shahani; B Garudachari; Arun M Isloor; Kammasandra N Shivananda

doi:10.1107/S1600536811037500

. 2011 Sep 17;67(Pt 10):o2682. doi: 10.1107/S1600536811037500

2-(4-Chlorophenyl)-2-oxoethyl 4-hydroxybenzoate

Hoong-Kun Fun ^a,^*,^‡, Tara Shahani ^a, B Garudachari ^b, Arun M Isloor ^b, Kammasandra N Shivananda ^c

PMCID: PMC3201459 PMID: 22065030

Abstract

The title compound, C₁₅H₁₁ClO₄, consists of a chlorobenzene ring and a phenol ring which are linked together by a 1,4-dioxo-2-oxabutane-1,4-diyl group. The dihedral angle between the chlorobenzene and phenol rings is 65.70 (11)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into chains along [010].

Related literature

For background to phenacyl benzoate, see: Sheehan & Umezaw (1973 ▶); Gandhi et al. (1995 ▶); Huang et al. (1996 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₁ClO₄
M _r = 290.69
Monoclinic,
a = 5.5307 (10) Å
b = 8.1324 (15) Å
c = 14.857 (2) Å
β = 95.120 (4)°
V = 665.57 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.56 × 0.23 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.852, T _max = 0.981
6399 measured reflections
3571 independent reflections
2457 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.106
S = 1.02
3571 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1511 Friedel pairs
Flack parameter: −0.20 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037500/bq2305sup1.cif

e-67-o2682-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037500/bq2305Isup2.hkl

e-67-o2682-Isup2.hkl^{(175.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037500/bq2305Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3ⁱ	0.78 (4)	2.01 (4)	2.783 (3)	168 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Phenacyl benzoate is a derivative of an acid formed by reaction between an acid and phenacyl bromide. These compounds find applications in the field of synthetic chemistry (Huang et al., 1996; Gandhi et al., 1995) such as in the synthesis of oxazoles, imidazoles, and benzoxazepines. They are also useful for photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound was synthesized to study its crystal structure.

The title compound, (Fig. 1), consists of a chlorobenzene (Cl1/C1–C6) ring and a phenol(O4/C10–C15) ring which are linked together by a 2-oxopropyl acetate (C7–C9/O1–O3) group. The dihedral angle formed between the chlorobenzene and a phenol ring is 65.70 (11) °. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), intermolecular O4—H1O4···O3 hydrogen bonds (Table 1) link the molecules in one-dimensional chains along [010].

Experimental

The mixture of 4-hydroxybenzoic acid (1.0 g, 0.0072 mol), potassium carbonate (1.10 g, 0.0079 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.68 g, 0.0072 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle-shaped 2-(4-chlorophenyl)-2-oxoethyl 4-hydroxybenzoate begin to separate out. It was collected by filtration and recrystallized from ethanol. Yield: 1.95 g, 92.8%, M.p: 453–454 K.