cis-4-(Tosyl­oxymeth­yl)cyclo­hexa­ne­carboxylic acid

De-Hong Jiang; Zhi-Hua Mao; Hu Zheng

doi:10.1107/S1600536808003176

. 2008 Feb 15;64(Pt 3):o598. doi: 10.1107/S1600536808003176

cis-4-(Tosyloxymethyl)cyclohexanecarboxylic acid

De-Hong Jiang ^a, Zhi-Hua Mao ^b, Hu Zheng ^a,^*

PMCID: PMC2960809 PMID: 21201936

Abstract

The title compound, C₁₅H₂₀O₅S, is an intermediate in the synthesis of novel aminocarboxylic acid derivatives. The cyclohexane ring exhibits a chair conformation. In the crystal structure, adjacent molecules form dimers via O—H⋯O hydrogen bonds.

Related literature

For the use of aminocarboxylic acid derivatives as anti-ulcer agents, see: Hoshina et al. (1984 ▶). For related structures, see: Qi et al. (2008 ▶); van Koningsveld et al. (1972 ▶).

Experimental

Crystal data

C₁₅H₂₀O₅S
M _r = 312.37
Monoclinic,
a = 12.545 (4) Å
b = 10.085 (3) Å
c = 12.654 (6) Å
β = 98.05 (3)°
V = 1585.1 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 291 (2) K
0.45 × 0.40 × 0.38 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
4142 measured reflections
2931 independent reflections
1794 reflections with I > 2σ(I)
R _int = 0.004
3 standard reflections every 250 reflections intensity decay: 0.8%

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.130
S = 1.03
2931 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003176/zl2098sup1.cif

e-64-0o598-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003176/zl2098Isup2.hkl

e-64-0o598-Isup2.hkl^{(143.9KB, hkl)}

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
O5—H5⋯O4ⁱ	0.82	1.83	2.642 (3)	173

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Some aminocarboxylic acid derivatives are used as anti-ulcer agents (Hoshina et al., 1984). To find new anti-ulcer agents, a series of trans/cis-cyclohexanecarboxylic acid derivatives were designed and synthesized.

In this paper, we want to report the synthesis and structure of the title compound, cis-4-(tosyloxymethyl)cyclohexanecarboxylic acid.

The cyclohexane ring exhibits a chair conformation and the cyclohexane C—C bond lengths and C—C—C endocyclic angles are in the range found for similar compounds (van Koningsveld, 1972) (Fig.1). They agree well with those of trans-4-(tosyloxymethyl)cyclohexanecarboxylic acid (Qi et al., 2008).

In the crystal structure, two molecules form centrosymmetric dimers via O—H···O hydrogen bonds (Fig. 2).

Experimental

cis-4-(Methoxycarboxyl)cyclohexanemethanol (10 mmol), pyridine (11 mmol) and a small amount of 4-dimethylaminopyridine were dissolved in dichloromethane (20 ml), then p-toluenesulfonyl chloride (11 mmol) was added dropwise with vigorous stirring at room temperature. After 8 h the reaction was quenched by addition of water and the organic layer separated was evaporated under vacuum, the solid obtained was hydrolyzed in a mixed solution of methanol and aqueous NaOH (11 mmol) for 4 h at 323 K. The title compound was then obtained by acidification with hydrochloric acid followed by recrystallization from ethyl acetate. Colorless crystals suitable for X-ray analysis were obtained by slow evaporation in ethyl acetate at room temperature.