2,6-Di-tert-butyl-4-(dimethyl­amino­meth­yl)phenol

Tao Zeng; Yu-Ping Hou

doi:10.1107/S1600536807065117

. 2007 Dec 6;64(Pt 1):o215. doi: 10.1107/S1600536807065117

2,6-Di-tert-butyl-4-(dimethylaminomethyl)phenol

Tao Zeng ^a,^*, Yu-Ping Hou ^b

PMCID: PMC2915276 PMID: 21200781

Abstract

The title compound, C₁₇H₂₉NO, is an important hindered phenol derivative. The asymmetric unit contains two molecules. Molecules interact through O—H⋯N hydrogen bonds to form a tetramer arranged around a twofold rotation axis.

Related literature

For related literature, see: Ciba-Geigy AG (1978 ▶); Eggensperger et al. (1974 ▶, 1976 ▶); Yamazaki & Seguchi (1997 ▶). For the synthesis, see: Coffield (1965 ▶); Coffield & Mich (1965 ▶); Rieker et al. (1968 ▶).

Experimental

Crystal data

C₁₇H₂₉NO
M _r = 263.41
Monoclinic,
a = 28.731 (9) Å
b = 8.912 (3) Å
c = 16.112 (5) Å
β = 122.965 (5)°
V = 3461.4 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 294 (2) K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.978, T _max = 0.989
6903 measured reflections
3752 independent reflections
2317 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.112
S = 0.99
3752 reflections
359 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065117/dn2296sup1.cif

e-64-0o215-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065117/dn2296Isup2.hkl

e-64-0o215-Isup2.hkl^{(337.8KB, 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—H1⋯N2	0.85	2.20	2.836 (3)	132
O2—H2⋯N1ⁱ	0.86	2.26	2.933 (3)	135

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support from the Start Foundation for Doctors (HY07116) of Yantai University.

supplementary crystallographic information

Comment

Hindered phenol antioxidants are widely used in polymers and lubricants. It could protect polymers by increasing both their process stability and long-term stability against oxidative degradation (Yamazaki & Seguchi, 1997). Moreover, ester of 3,5-di-tert-butyl-4-hydroxyphenol acetic acid is one important kind of antioxidant derivative. An important route to prepare these compounds is to react an α-halo ester compound with the title compound in the presence of a strong base (Eggensperger et al., 1974, 1976; Eggensperger et al., 1976; Ciba-Geigy AG, 1978). The title compound is ususlly called a Mannich base. The title compound was prepared from 4-bromomethyl-2,6-di-tert-butyl-phenol and N,N-dimethylamine.It can also be easily obtained by a Mannich reaction from 2,6-di-tert-butylphenol,formaldehyde and dimethylamine (Coffield, 1965; Coffield & Mich, 1965).

The asymmetric unit of the title compound contains two molecules which are linked by a weak O—H···N hydrogen bond (Fig. 1). Each pseudo dimer interacts with a symmetry related one to build up like a crown arranged around axis parallele to the b axis through O—H··· hydrogen bonds (Table 1, Fig. 2).

Experimental

The 4-bromomethyl-2,6-di-tert-butyl-phenol was synthesized according to the method described by Rieker(Rieker et al.,1968). Dimethylamine (2.7 g, 0.06 mol) and 4-bromomethyl-2,6-di-tert-butyl-phenol (9.0 g, 0.03 mol) were added, with stirring to THF(60 ml)at 273 K. The reaction mixture was stirred at 273 K for a further 2 h. The solvent THF was evaporated under reduced pressure and the residual was washed with water (30 ml). The product (7.39 g) was obtained in a yield of 93.6%. Suitable crystals were obtained by slow evaporation of a mixture of ethyl acetate and ethanol.