1-(4-Benz­yloxy-2-hy­droxy­phen­yl)ethanone

Ma, Y.-T.; Yang, C.-L.; Li, Z.-S.; Li, Z.-Q.; Ding, J.-N.

doi:10.1107/S160053681104637X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3225

https://doi.org/10.1107/S160053681104637X

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1-(4-Benzyloxy-2-hydroxyphenyl)ethanone

Ya-Tuan Ma,^a,^b ^* Chong-Lin Yang,^b Zhen-Shuo Li,^b Zhong-Qiang Li ^b and Juan-Ning Ding ^b

^aCollege of Life Sciences, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China
^*Correspondence e-mail: mnathantuan@yahoo.com

(Received 11 October 2011; accepted 3 November 2011; online 9 November 2011)

The title compound, C₁₅H₁₄O₃, has been obtained from the reaction of 2,4-dihydroxyacetophenone, potassium carbonate and benzyl bromide. The remaining hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond. In the crystal, intermolecular C—H⋯O contacts occur.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ). For synthetic procedures for related compounds, see: Mendelson et al. (1996 ). For a related structure, see: Ma et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₄O₃
M_r = 242.26
Triclinic, $[P \overline 1]$
a = 5.8433 (7) Å
b = 8.0096 (8) Å
c = 13.8089 (13) Å
α = 74.061 (1)°
β = 84.589 (1)°
γ = 87.372 (2)°
V = 618.54 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.987
3169 measured reflections
2167 independent reflections
1291 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.114
S = 1.02
2167 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.84	2.554 (2)	146
C1—H1B⋯O2ⁱ	0.96	2.52	3.408 (3)	154
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104637X/im2328sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104637X/im2328Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104637X/im2328Isup3.cml

checkCIF report

Comment top

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the employment of an alkali-metal salt of the hydroxy compound and an alkyl halide (Dermer, 1934). Synthetic procedures to ethers derived from 2,4-dihydroxy-acetophenone as well as the structural characterisation of a related molecule have been described before (Mendelson et al., 1996; Ma et al., 2010).

In this paper, we present the title compound, (I), which was synthesized by the reaction of 2, 4-dihydroxy-acetonephenone, potassium carbonate and benzyl bromide. In (I) (Fig. 1), the dihedral angle between the aromatic rings is 53.48 (4)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For synthetic procedures for related compounds, see: Mendelson et al. (1996). For a related structure, see: Ma et al. (2010).

Experimental top

2, 4-Dihydroxy-acetonephenone (4 mmol), potassium carbonate (8 mmol), benzyl bromide (4 mmol), and 40 ml acetone were mixed in a 100 ml flask. After 3 h stirring at 331 K, the crude product was obtained (yield: 78%). Single crystals were obtained by recrystallization from methanol.

Structure description top

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For synthetic procedures for related compounds, see: Mendelson et al. (1996). For a related structure, see: Ma et al. (2010).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Sheldrick, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of (I) viewed along the b axis, with hydrogen bonds shown as dashed lines.

1-(4-Benzyloxy-2-hydroxyphenyl)ethanone top

Crystal data top

C₁₅H₁₄O₃	Z = 2
M_r = 242.26	F(000) = 256
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Melting point = 378–379 K
a = 5.8433 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0096 (8) Å	Cell parameters from 945 reflections
c = 13.8089 (13) Å	θ = 2.7–25.4°
α = 74.061 (1)°	µ = 0.09 mm⁻¹
β = 84.589 (1)°	T = 298 K
γ = 87.372 (2)°	Triclinic, colourless
V = 618.54 (11) Å³	0.23 × 0.20 × 0.15 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2167 independent reflections
Radiation source: fine-focus sealed tube	1291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.980, T_max = 0.987	k = −9→9
3169 measured reflections	l = −16→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
2167 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₅H₁₄O₃	γ = 87.372 (2)°
M_r = 242.26	V = 618.54 (11) Å³
Triclinic, P1	Z = 2
a = 5.8433 (7) Å	Mo Kα radiation
b = 8.0096 (8) Å	µ = 0.09 mm⁻¹
c = 13.8089 (13) Å	T = 298 K
α = 74.061 (1)°	0.23 × 0.20 × 0.15 mm
β = 84.589 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2167 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1291 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.026
3169 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
2167 reflections	Δρ_min = −0.14 e Å⁻³
165 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.6013 (3)	0.8182 (2)	−0.02477 (10)	0.0812 (5)
O2	0.8544 (3)	0.91909 (18)	0.08846 (10)	0.0723 (5)
H2	0.8070	0.9162	0.0349	0.108*
O3	0.6839 (2)	0.71044 (16)	0.44284 (9)	0.0584 (4)
C1	0.2766 (4)	0.6428 (3)	0.03392 (16)	0.0804 (7)
H1A	0.2655	0.6613	−0.0372	0.121*
H1B	0.1382	0.6848	0.0635	0.121*
H1C	0.2971	0.5210	0.0653	0.121*
C2	0.4770 (4)	0.7384 (3)	0.04958 (16)	0.0627 (6)
C3	0.5296 (3)	0.7344 (2)	0.15150 (13)	0.0499 (5)
C4	0.7175 (3)	0.8243 (2)	0.16617 (13)	0.0529 (5)
C5	0.7750 (3)	0.8181 (2)	0.26222 (13)	0.0520 (5)
H5	0.9021	0.8771	0.2705	0.062*
C6	0.6417 (3)	0.7236 (2)	0.34562 (13)	0.0479 (5)
C7	0.4525 (3)	0.6338 (2)	0.33393 (14)	0.0544 (5)
H7	0.3636	0.5700	0.3902	0.065*
C8	0.3993 (3)	0.6409 (2)	0.23848 (14)	0.0566 (5)
H8	0.2719	0.5815	0.2310	0.068*
C9	0.8747 (3)	0.8038 (3)	0.45748 (14)	0.0605 (6)
H9A	0.8578	0.9257	0.4220	0.073*
H9B	1.0162	0.7594	0.4301	0.073*
C10	0.8863 (3)	0.7845 (2)	0.56755 (14)	0.0501 (5)
C11	0.7172 (3)	0.8552 (3)	0.62181 (15)	0.0618 (6)
H11	0.5887	0.9088	0.5905	0.074*
C12	0.7353 (4)	0.8478 (3)	0.72185 (15)	0.0655 (6)
H12	0.6197	0.8961	0.7574	0.079*
C13	0.9239 (4)	0.7690 (3)	0.76880 (16)	0.0654 (6)
H13	0.9373	0.7646	0.8360	0.078*
C14	1.0919 (4)	0.6970 (3)	0.71643 (17)	0.0688 (6)
H14	1.2196	0.6430	0.7482	0.083*
C15	1.0730 (4)	0.7039 (3)	0.61631 (15)	0.0606 (6)
H15	1.1878	0.6535	0.5815	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1067 (13)	0.0896 (12)	0.0446 (9)	0.0045 (10)	−0.0021 (9)	−0.0160 (8)
O2	0.0836 (10)	0.0796 (11)	0.0449 (8)	−0.0142 (8)	0.0097 (7)	−0.0051 (7)
O3	0.0708 (9)	0.0625 (9)	0.0418 (8)	−0.0226 (7)	−0.0022 (6)	−0.0115 (6)
C1	0.0932 (18)	0.0912 (18)	0.0669 (15)	0.0076 (15)	−0.0257 (13)	−0.0336 (13)
C2	0.0768 (16)	0.0593 (14)	0.0544 (14)	0.0154 (12)	−0.0087 (12)	−0.0211 (11)
C3	0.0601 (13)	0.0478 (12)	0.0422 (12)	0.0036 (10)	−0.0029 (9)	−0.0139 (9)
C4	0.0627 (14)	0.0488 (12)	0.0410 (12)	0.0001 (10)	0.0065 (10)	−0.0057 (9)
C5	0.0569 (13)	0.0515 (12)	0.0464 (12)	−0.0099 (10)	−0.0014 (10)	−0.0106 (9)
C6	0.0593 (12)	0.0441 (11)	0.0385 (11)	−0.0048 (10)	0.0007 (9)	−0.0096 (9)
C7	0.0612 (13)	0.0548 (13)	0.0461 (12)	−0.0141 (10)	0.0056 (10)	−0.0134 (9)
C8	0.0581 (13)	0.0589 (13)	0.0558 (13)	−0.0075 (10)	−0.0035 (10)	−0.0202 (10)
C9	0.0640 (14)	0.0650 (14)	0.0533 (13)	−0.0178 (11)	−0.0017 (10)	−0.0158 (10)
C10	0.0537 (12)	0.0511 (12)	0.0466 (12)	−0.0088 (10)	−0.0041 (10)	−0.0137 (9)
C11	0.0546 (13)	0.0719 (15)	0.0578 (14)	0.0027 (11)	−0.0098 (10)	−0.0147 (11)
C12	0.0641 (14)	0.0770 (16)	0.0577 (14)	−0.0032 (12)	0.0022 (11)	−0.0245 (11)
C13	0.0768 (16)	0.0720 (16)	0.0485 (13)	−0.0132 (13)	−0.0077 (12)	−0.0158 (11)
C14	0.0660 (15)	0.0761 (16)	0.0606 (15)	0.0005 (12)	−0.0168 (12)	−0.0088 (12)
C15	0.0606 (14)	0.0612 (14)	0.0595 (14)	0.0012 (11)	0.0002 (11)	−0.0178 (10)

Geometric parameters (Å, º) top

O1—C2	1.238 (2)	C7—H7	0.9300
O2—C4	1.347 (2)	C8—H8	0.9300
O2—H2	0.8200	C9—C10	1.493 (2)
O3—C6	1.362 (2)	C9—H9A	0.9700
O3—C9	1.430 (2)	C9—H9B	0.9700
C1—C2	1.491 (3)	C10—C15	1.377 (3)
C1—H1A	0.9600	C10—C11	1.379 (3)
C1—H1B	0.9600	C11—C12	1.380 (2)
C1—H1C	0.9600	C11—H11	0.9300
C2—C3	1.460 (3)	C12—C13	1.371 (3)
C3—C4	1.400 (3)	C12—H12	0.9300
C3—C8	1.404 (2)	C13—C14	1.365 (3)
C4—C5	1.386 (2)	C13—H13	0.9300
C5—C6	1.383 (2)	C14—C15	1.383 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.392 (2)	C15—H15	0.9300
C7—C8	1.368 (2)

C4—O2—H2	109.5	C7—C8—H8	118.8
C6—O3—C9	117.04 (14)	C3—C8—H8	118.8
C2—C1—H1A	109.5	O3—C9—C10	109.89 (15)
C2—C1—H1B	109.5	O3—C9—H9A	109.7
H1A—C1—H1B	109.5	C10—C9—H9A	109.7
C2—C1—H1C	109.5	O3—C9—H9B	109.7
H1A—C1—H1C	109.5	C10—C9—H9B	109.7
H1B—C1—H1C	109.5	H9A—C9—H9B	108.2
O1—C2—C3	120.3 (2)	C15—C10—C11	118.14 (18)
O1—C2—C1	119.2 (2)	C15—C10—C9	120.72 (17)
C3—C2—C1	120.5 (2)	C11—C10—C9	121.03 (18)
C4—C3—C8	116.92 (17)	C10—C11—C12	121.11 (19)
C4—C3—C2	120.48 (19)	C10—C11—H11	119.4
C8—C3—C2	122.6 (2)	C12—C11—H11	119.4
O2—C4—C5	116.22 (19)	C13—C12—C11	119.94 (19)
O2—C4—C3	122.26 (17)	C13—C12—H12	120.0
C5—C4—C3	121.51 (17)	C11—C12—H12	120.0
C6—C5—C4	119.41 (19)	C14—C13—C12	119.7 (2)
C6—C5—H5	120.3	C14—C13—H13	120.2
C4—C5—H5	120.3	C12—C13—H13	120.2
O3—C6—C5	123.69 (18)	C13—C14—C15	120.3 (2)
O3—C6—C7	115.64 (16)	C13—C14—H14	119.8
C5—C6—C7	120.67 (17)	C15—C14—H14	119.8
C8—C7—C6	119.02 (18)	C10—C15—C14	120.81 (19)
C8—C7—H7	120.5	C10—C15—H15	119.6
C6—C7—H7	120.5	C14—C15—H15	119.6
C7—C8—C3	122.5 (2)

O1—C2—C3—C4	1.6 (3)	C5—C6—C7—C8	−0.3 (3)
C1—C2—C3—C4	−179.90 (17)	C6—C7—C8—C3	0.5 (3)
O1—C2—C3—C8	−177.70 (18)	C4—C3—C8—C7	−1.0 (3)
C1—C2—C3—C8	0.8 (3)	C2—C3—C8—C7	178.29 (16)
C8—C3—C4—O2	−179.70 (16)	C6—O3—C9—C10	176.25 (14)
C2—C3—C4—O2	1.0 (3)	O3—C9—C10—C15	117.1 (2)
C8—C3—C4—C5	1.3 (3)	O3—C9—C10—C11	−66.5 (2)
C2—C3—C4—C5	−178.00 (16)	C15—C10—C11—C12	0.9 (3)
O2—C4—C5—C6	179.84 (16)	C9—C10—C11—C12	−175.56 (18)
C3—C4—C5—C6	−1.1 (3)	C10—C11—C12—C13	0.0 (3)
C9—O3—C6—C5	1.4 (2)	C11—C12—C13—C14	−0.6 (3)
C9—O3—C6—C7	−178.88 (15)	C12—C13—C14—C15	0.3 (3)
C4—C5—C6—O3	−179.73 (15)	C11—C10—C15—C14	−1.2 (3)
C4—C5—C6—C7	0.6 (3)	C9—C10—C15—C14	175.30 (19)
O3—C6—C7—C8	−179.99 (15)	C13—C14—C15—C10	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.84	2.554 (2)	146
C1—H1B···O2ⁱ	0.96	2.52	3.408 (3)	154

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₃
M_r	242.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.8433 (7), 8.0096 (8), 13.8089 (13)
α, β, γ (°)	74.061 (1), 84.589 (1), 87.372 (2)
V (Å³)	618.54 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.20 × 0.15

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	3169, 2167, 1291
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.114, 1.02
No. of reflections	2167
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.84	2.554 (2)	146
C1—H1B···O2ⁱ	0.96	2.52	3.408 (3)	154

Symmetry code: (i) x−1, y, z.

Acknowledgements

We would like to acknowledge funding support by Shaanxi Province Science and Technology (under contract No. 2011 K02–07) and the Program of Northwest A&F University (No. Z111020908).

References

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