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Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7

  • Xiao-ming Shang , Ying Luo , Nuo Chen , Zong-de Wang and Hai Luo ORCID logo EMAIL logo
Published/Copyright: November 14, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 1

Abstract

C14H18O7, orthorhombic, P212121 (no. 19), a = 4.3538(6) Å, b = 12.7630(19) Å, c = 26.493(4) Å, V = 1,472.2(4) Å3, Z = 4, R gt (F) = 0.0414, wR ref (F 2) = 0.1043, T = 296(2) K.

CCDC no.: 2393676

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.19 × 0.15 × 0.13 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 11,557, 2,748, 0.039
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1960
N(param)refined: 194
Programs: Bruker, 1 SHELX, 2 , 3 Diamond 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.2531 (12) 0.3586 (3) −0.03413 (10) 0.0820 (13)
H1A 0.0477 0.3582 −0.0473 0.123*
H1B 0.3596 0.2970 −0.0454 0.123*
H1C 0.3591 0.4198 −0.0459 0.123*
C2 0.0917 (9) 0.4383 (2) 0.04178 (12) 0.0579 (9)
C3 0.1012 (8) 0.4357 (2) 0.09784 (10) 0.0474 (8)
C4 0.2571 (8) 0.3577 (2) 0.12362 (10) 0.0468 (8)
H4 0.3544 0.3041 0.1060 0.056*
C5 0.2670 (7) 0.3602 (2) 0.17595 (10) 0.0441 (7)
C6 0.1262 (7) 0.4418 (2) 0.20184 (10) 0.0417 (7)
C7 −0.0367 (8) 0.5184 (2) 0.17540 (11) 0.0458 (8)
C8 −0.0497 (8) 0.5149 (2) 0.12334 (10) 0.0489 (8)
H8 −0.1591 0.5655 0.1056 0.059*
C9 0.5440 (10) 0.1986 (3) 0.18127 (12) 0.0674 (10)
H9A 0.3864 0.1596 0.1643 0.101*
H9B 0.6408 0.1550 0.2061 0.101*
H9C 0.6943 0.2215 0.1572 0.101*
C10 −0.3476 (9) 0.6719 (2) 0.17966 (12) 0.0619 (9)
H10A −0.2196 0.7096 0.1564 0.093*
H10B −0.4303 0.7197 0.2041 0.093*
H10C −0.5126 0.6391 0.1616 0.093*
C11 −0.0880 (7) 0.4045 (2) 0.28092 (10) 0.0500 (8)
H11A −0.0901 0.3292 0.2758 0.060*
H11B −0.2820 0.4326 0.2691 0.060*
C12 −0.0486 (8) 0.4284 (2) 0.33539 (11) 0.0471 (8)
C13 −0.2301 (10) 0.3800 (3) 0.41709 (10) 0.0693 (11)
H13A −0.3647 0.4389 0.4239 0.083*
H13B −0.0278 0.3963 0.4302 0.083*
C14 −0.3509 (11) 0.2845 (3) 0.44159 (12) 0.0866 (13)
H14A −0.5495 0.2683 0.4279 0.130*
H14B −0.3682 0.2962 0.4773 0.130*
H14C −0.2134 0.2271 0.4355 0.130*
O1 0.2427 (6) 0.35965 (16) 0.02034 (7) 0.0672 (7)
O2 −0.0373 (9) 0.5048 (2) 0.01778 (8) 0.1019 (12)
O3 −0.1698 (6) 0.59389 (17) 0.20468 (7) 0.0590 (6)
O4 0.1574 (5) 0.44972 (15) 0.25340 (7) 0.0471 (5)
O5 0.4110 (6) 0.28758 (16) 0.20538 (7) 0.0570 (6)
O6 0.0991 (8) 0.4973 (2) 0.35315 (8) 0.0834 (9)
O7 −0.2130 (6) 0.36104 (16) 0.36309 (7) 0.0593 (6)

1 Source of materials

The mixture of methyl 4-hydroxy-3,5-dimethoxybenzoate (2.12 g, 0.01 mol), ethyl bromoacetate (2.03 g, 0.012 mol), K2CO3 (2.76 g, 0.02 mol) and acetone (15 mL) was reacted at 70 °C for 24 h. After the reaction was completed (monitored by TLC), colorless crystals were obtained by slow cooling. The product was filtered, and washed with water 3 times respectively. Yield 90 % (based on methyl 4-hydroxybenzoate). Elemental Anal. Calcd. (%) for C14H18O7 (298.29): C, 56.37; H, 6.08. Found (%): C, 55.53; H, 6.16.

2 Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with U iso(H) = 1.5 U eq(C) for methyl H atoms and 1.2 U eq(C) for all other H atoms.

3 Comment

Syringic acid, 4-hydroxy-3,5-dimethoxybenzoic acid, is a phenolic acid of benzoic acid categorie, which has antibacterial activities, sedative activities and local anesthetic effects. 5 , 6 , 7 , 8 Methyl syringate is considered as a symbolic component of Manuka honey, and it is also a functional component of its antioxidant and antibacterial activity. 9 , 10 , 11 It also is an effective bacterial and fungal laccase phenol medium and an agonist of TRPA1. 12 Because of its strong activities and its wide applications, the synthesis and application of syringic acid derivatives have attracted much attention. 13 , 14 Saeed et al. have reported the synthesis and crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate. 15 Nie et al. have reported the synthesis and crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate. 16 We still focused on the synthesis and antibacterial activities of preservatives.

In the molecules of the title structure bond lengths and angles are very similar to those given in the literature. 15 , 16 , 17 In the title structure, the part of methyl 4-hydroxy-3,5-dimethoxybenzoic acid is approximately planar. The dihedral angle formed by the C3–C8 plane with the carboxlate group O1–C2–O2 plane is 2.5°. The torsion angles of C4–C5–O5–C9 and C8–C7–O3–C10 are −4.5(4)° and 3.2(4)°. The part of 2-ethoxy-2-oxoethoxy group is perpendicular to methyl 4-hydroxy-3,5-dimethoxybenzoic acid and the torsion angles of C5–C6–O4–C11, C6–O4–C11–C12 and C12–O7–C13–C14 are −95.6(3)°, −173.5(2)° and −165.8(3)°. The dihedral angle formed by the C3–C8 plane with the carboxylate group O6–C12–O7 plane is 71.218(107)°.

Corresponding author: Hai Luo, East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, Jiangxi Provincial Key Laboratory of Improved Variety Breeding and Efficient Utilization of Native Tree Species, College of Forestry, Jiangxi Agricultural University, Nanchang, 330045, People’s Republic of China and The Key Laboratory of State Forestry and Grassland Administration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, Kunming, 650224, People’s Republic of China, E-mail:

Acknowledgments

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This research was supported by the National Natural Science Foundation of China (Grant Number 32360365), the Key Laboratory of State Forestry and Grassland Administration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China (Grant Number 2022–KF12).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2024-10-01
Accepted: 2024-10-25
Published Online: 2024-11-14
Published in Print: 2025-02-25

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
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  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
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  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
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  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
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  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
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https://doi.org/10.1515/ncrs-2024-0387
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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