2,4-Di-tert-butyl-6-[1-(3,5-di-tert-butyl-2-hydroxy­phen­yl)eth­yl]phenyl 4-methyl­benzene­sulfonate

Jincai Wu; Xiaobo Pan; Lei Wang; Lihui Yao

doi:10.1107/S1600536808042323

. 2008 Dec 17;65(Pt 1):o155. doi: 10.1107/S1600536808042323

2,4-Di-tert-butyl-6-[1-(3,5-di-tert-butyl-2-hydroxyphenyl)ethyl]phenyl 4-methylbenzenesulfonate

Jincai Wu ^a,^*, Xiaobo Pan ^a, Lei Wang ^a, Lihui Yao ^a

PMCID: PMC2968069 PMID: 21581613

Abstract

The title compound, C₃₇H₅₂O₄S, was obtained by the reaction of 6,6′-(ethane-1,1-diyl)bis(2,4-di-tert-butylphenol) and 4-methylbenzene-1-sulfonyl chloride. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond. Two of the tert-butyl groups are disordered over two sets of sites with occupancies 0.530 (15)/0.470 (15) and 0.615 (11)/0.385 (11).

Related literature

For the polymerization of cyclic esters, see: Endo et al. (1987 ▶); Wu et al. (2006 ▶). graphic file with name e-65-0o155-scheme1.jpg

Experimental

Crystal data

C₃₇H₅₂O₄S
M _r = 592.85
Monoclinic,
a = 13.893 (2) Å
b = 15.760 (2) Å
c = 17.525 (3) Å
β = 107.262 (3)°
V = 3664.3 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 (2) K
0.32 × 0.28 × 0.25 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.962, T _max = 0.970
18079 measured reflections
6422 independent reflections
4281 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.157
S = 1.06
6422 reflections
435 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042323/bt2830sup1.cif

e-65-0o155-sup1.cif^{(35KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042323/bt2830Isup2.hkl

e-65-0o155-Isup2.hkl^{(314.3KB, 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
O1—H1A⋯O4	0.82	2.30	3.036 (2)	150

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Acknowledgments

We are grateful for the financial support of the National Science Foundation of China (20601011) and Science Foundation of Gansu Province of China (0803RJZA103).

supplementary crystallographic information

Comment

In past decades, significant advance have been made in polymerization of cyclic esters, such as poly(e-caprolactone) (Endo et al., 1987) or poly(lactide) (Wu et al., 2006). A particularly convenient method for the synthesis of polylactides is the ring-opening polymerization (ROP) of lactides. Due to the advantages of well controlled molecular weight and low polydispersity, many metal complexes have been used. In the present study, we report a compound, which is a potential ligand for investigation of ring-opening polymerization of lactides. The bond lengths and angles are within normal ranges. There is a intramolecular hydrogen bond.

Experimental

6,6'-(ethane-1,1-diyl)bis(2,4-di-tert-butylphenol) (4.38 g, 10 mmol) and triethylamine (14 mL, 100 mmol) were dissolved in 100 ml of dichloromethane. 4-Methylbenzene-1-sulfonyl chloride (2.09 g, 11 mmol) in dichloromethane (20 ml) was added dropwise into the above solution at 0 °C for about 1 h. The resulting mixture was then stirred for 24 h while the temperature was increased to room temperature. The solution was filtered, and the filtrate was washed with 50 ml of water three times. The dichloromethane layer was collected and dried over anhydrous MgSO₄ and filtered through Celite again to remove MgSO₄. The resulting filtrate was then dried under vacuum, and the residue was recrystallized by slow cooling of a acetonitrile solution.