Pentyl (E)-3-(3,4-dihy­droxy­phen­yl)acrylate

Jun Wang; Shuangshuang Gu; Leixia Zhang; Fuan Wu; Xijie Guo

doi:10.1107/S1600536811040499

. 2011 Oct 8;67(Pt 11):o2871. doi: 10.1107/S1600536811040499

Pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Jun Wang ^a,^*, Shuangshuang Gu ^a, Leixia Zhang ^a, Fuan Wu ^a,^b, Xijie Guo ^a,^b

PMCID: PMC3247606 PMID: 22219911

Abstract

In the molecule of the title compound, C₁₄H₁₈O₄, the C=C double bond is in an E configuration. The molecule is almost planar (r.m.s. deviation of all non-H atoms = 0.04 Å). An intramolecular O—H⋯O hydrogen bond occurs. In the crystal, intermolecular O—H⋯O interactions link the molecules into ribbons extending in [110].

Related literature

For general background to the biological activity of caffeic acid and its esters, see: Uwai et al. (2008 ▶); Buzzi et al. (2009 ▶); For the preparation, see: Xia et al. (2006 ▶); Son et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₈O₄
M _r = 250.28
Triclinic,
a = 5.3070 (11) Å
b = 10.567 (2) Å
c = 11.816 (2) Å
α = 90.96 (3)°
β = 91.84 (3)°
γ = 98.60 (3)°
V = 654.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.991
2703 measured reflections
2419 independent reflections
1627 reflections with I > 2σ(I)
R _int = 0.023
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.169
S = 1.00
2419 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040499/gw2109sup1.cif

e-67-o2871-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040499/gw2109Isup2.hkl

e-67-o2871-Isup2.hkl^{(118.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040499/gw2109Isup3.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
O1—H1B⋯O2	0.82	2.30	2.738 (2)	114
O1—H1B⋯O2ⁱ	0.82	2.15	2.840 (2)	142
O2—H2A⋯O3ⁱⁱ	0.82	1.98	2.800 (2)	173
C5—H5A⋯O3ⁱⁱ	0.93	2.52	3.230 (3)	133

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was sponsored by the Qing Lan Project of Jiangsu Province, the Natural Science Foundation of Jiangsu Province (BK2009213), the College Natural Science Research Project of Jiangsu Province (08KJB530002), the Science and Technology Support Program of Jiangsu Province (BE2010419), the Start Project for Introducing Talent of Jiangsu University of Science and Technology (35211002), the Pre-research for NSFC Project of Jiangsu University of Science and Technology (33201002) and the earmarked fund for Modern Agro-industry Technology Research Systems.

supplementary crystallographic information

Comment

Caffeic acid and its esters have been a research hot spot for a long time. These compounds are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities (Uwai et al., 2008; Buzzi et al., 2009). As a part of our studies into the synthesis of caffeic acid derivatives, the title compound (1) pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate was synthesized (Xia et al. (2006); Son et al. (2011)). We report herein the crystal structure of the title compound.

The molecule of (I) has an E configuration (Fig. 1); All non-H atoms of (I) are almost coplanar, with a root mean square deviating from the least-squares plane of 0.04 A°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, hydroxy groups contribute to intermolecular O—H···O interactions (Table 1) link the molecules into ribbons extended in the [110] direction (Fig. 2), in which they may be effective in the stabilization of thestructure. On the other hand, the intramolecular O—H···O H-bond also contribute to the stability of the molecular configuration (Fig. 1 and Table 1).

Experimental

Esterification of caffeic acid with amyl alcohol was performed in a column (inner diameter= 15 mm, length = 200 mm). Caffeic acid (8.95 g, 0.05 mol) was dissolved in amyl alcohol (100 ml). The mixture was stirred at 80°C for 60 minutes and fed from the top of the reactor with syringe pumps. The feed rate of the mixture was fixed at 10.0 ml/h. Cation exchange resin CD-552 particles(5 g) and molecular sieve(5 g) were packed into the middle of the reactor and glass beads of 2 mm in diameter were loaded into the rest of the column. The reaction temperature continued at 90°C for 20 h. The mixture was evaporated to dryness and followed by the addition of ethanol and extracted with chloroform three times. The chloroform extract was dried over evaporated to give a solid residue, and dissolved in ethanol/petroleum ether (1:1) to crystal. The solution was filtered and concentrated to yield a brown crystalline product (5.3 g, 59.2%). Recrystallization from ethanol gave colourless crystal.