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[ CAS No. 26153-38-8 ]

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Chemical Structure| 26153-38-8
Chemical Structure| 26153-38-8
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CAS No. :26153-38-8 MDL No. :MFCD00016611
Formula : C7H6O3 Boiling Point : 324.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :138.12 g/mol Pubchem ID :94365
Synonyms :

Safety of [ 26153-38-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26153-38-8 ]

  • Upstream synthesis route of [ 26153-38-8 ]
  • Downstream synthetic route of [ 26153-38-8 ]

[ 26153-38-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 7311-34-4 ]
  • [ 26153-38-8 ]
Reference: [1] Patent: CN107951870, 2018, A, . Location in patent: Paragraph 0032; 0037; 0038
  • 2
  • [ 29654-55-5 ]
  • [ 26153-38-8 ]
Reference: [1] Journal of Materials Chemistry, 2000, vol. 10, # 4, p. 867 - 871
  • 3
  • [ 501-36-0 ]
  • [ 26153-38-8 ]
  • [ 1332302-64-3 ]
  • [ 123-08-0 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 18, p. 4846 - 4849
  • 4
  • [ 856077-23-1 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1921, vol. <2> 101, p. 94
  • 5
  • [ 35354-29-1 ]
  • [ 26153-38-8 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1399,1412-1421[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 4212
[3] Chemische Berichte, 1941, vol. 74, p. 869,872
  • 6
  • [ 102-61-4 ]
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Reference: [1] Advances in Chemistry Series, 1959, vol. 21, p. 149,151
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  • [ 861532-85-6 ]
  • [ 26153-38-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1921, vol. <2> 101, p. 94
  • 8
  • [ 501-36-0 ]
  • [ 10083-24-6 ]
  • [ 26153-38-8 ]
  • [ 99-10-5 ]
  • [ 123-08-0 ]
Reference: [1] Rapid Communications in Mass Spectrometry, 2010, vol. 24, # 5, p. 634 - 642
[2] Biochimie, 2012, vol. 94, # 3, p. 741 - 747
  • 9
  • [ 501-36-0 ]
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  • [ 400608-32-4 ]
  • [ 123-08-0 ]
Reference: [1] Photochemical and Photobiological Sciences, 2013, vol. 12, # 4, p. 638 - 644
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  • [ 65877-43-2 ]
  • [ 10028-15-6 ]
  • [ 64-19-7 ]
  • [ 621-59-0 ]
  • [ 26153-38-8 ]
Reference: [1] Yakugaku Zasshi, 1938, vol. 58, p. 405,410; dtsch. Ref. S. 83[2] Chem. Zentralbl., 1939, vol. 110, # I, p. 130
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  • [ 501-36-0 ]
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  • [ 400608-32-4 ]
  • [ 123-08-0 ]
Reference: [1] Photochemical and Photobiological Sciences, 2013, vol. 12, # 4, p. 638 - 644
  • 12
  • [ 26153-38-8 ]
  • [ 74-88-4 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
39% With potassium carbonate In N,N-dimethyl-formamide at -10℃; Inert atmosphere To a stirredsuspension of 3,5-dihydroxybenzaldehyde, 12 (2.76 g,20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF(50 mL) was added methyl iodide (1.25 mL, 20.0 mmol)dropwise at −10 C under nitrogen atmosphere. The mixturewas stirred for 3 h at this temperature. After completion of thereaction, water (70 mL) was added. The mixture was thenextracted with ether (2 × 80 mL), the combined organic layerwas washed with brine (2 × 80 mL), dried over anhydrousNa2SO4, filtered and the filtrate was concentrated in vacuo.The crude residue was purified by column chromatography(EtOAc/hexane = 1/4) to yield the compound 17 (1.19 g,39percent) as white solid. Rf = 0.23 (EtOAc/hexane = 1/4); mp128–130 C; 1H NMR (300 MHz, CDCl3) δ 9.86 (1H, s),6.98 (1H, dd, J = 2.4, 1.5 Hz), 6.95 (1H, dd, J = 2.4,1.5 Hz), 6.67 (1H, t, J = 2.4 Hz), 5.79 (1H, s), 3.84 (3H, s);13C NMR (75 MHz, CDCl3) δ 191.8, 161.3, 157.2, 138.4,109.0, 108.1, 107.0, 55.7.
39% With potassium carbonate In N,N-dimethyl-formamide at -10℃; for 3 h; Inert atmosphere To a suspension of 3,5-dihydroxybenzaldehyde (3,5-dihydroxybenzaldehyde, compound 12) (2.76 g, 20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF (50 mL) was added methyl iodide (1.25 mL, 20.0 mmol) in a nitrogen atmosphere, - 10°C. The reaction mixture was stirred at this temperature for three hours. After the reaction was completed, 70 ml of water was added. The reaction mixture was then extracted with ether (2 x 80 mL) and the combined organic layers were washed with brine (2 x 80 mL), dried over anhydrous Na2SO4,The filtrate was concentrated in vacuo. The crude compound was purified by column chromatography (EtOAc / hexane = 1/4) to obtain a white solid compound 17 (1.19 g, 39percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: at 20℃; for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at O0C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) was treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction was treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It was then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase was washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound was obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent)..
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
Synthesis of Compound 394; 3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).

Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2907 - 2914
[2] Patent: KR2016/115127, 2016, A, . Location in patent: Paragraph 0018; 0019
[3] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 359-360
[4] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 256
[5] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 359-360
[6] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 359-360
  • 13
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YieldReaction ConditionsOperation in experiment
25% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 0.5 h; a)
3 Hydroxy-5-methoxybenzaldehyde
Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0 °C.
The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid.
The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane / petroleum ether (2: 1 then 100: 0)) to give the title compound (309 mg, 25percent) as a gum. 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98 - 6.99 (m, 2 H), 6.94 - 6.96 (m, 1 H), 3.80 (s, 3 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 1, p. 1 - 4
[2] Patent: EP906091, 2006, B1, . Location in patent: Page/Page column 21
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  • [ 1972-28-7 ]
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YieldReaction ConditionsOperation in experiment
25% With triphenylphosphine In tetrahydrofuran; methanol; Petroleum ether a
3-Hydroxy-5-methoxybenzaldehyde
Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0° C.
The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid.
The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane/petroleum ether (2:1 then 100:0)) to give the title compound (309 mg, 25percent) as a gum. 1 H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98-6.99 (m, 2 H), 6.94-6.96 (m, 1 H), 3.80 (s, 3 H).
Reference: [1] Patent: US5891909, 1999, A,
  • 15
  • [ 26153-38-8 ]
  • [ 100-39-0 ]
  • [ 14615-72-6 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In acetone at 0 - 40℃; for 12 h; Inert atmosphere General procedure: To the stirred solution of phenolic aldehyde (2.00 mmol) in anhydrous acetone (10 mL) was added K2CO3 (3.00 mmol, 1.5 eq.) In a nitrogen atmosphere0 And cooled.Benzyl bromide (2.4 mmol, 1.2 eq.) Was slowly added,The mixture temperature was raised to 40 ,Stir for 12 hours.After completion of the reaction, the reaction mixture was cooled to room temperature,Filter through a Celite pad and concentrate in vacuo.The crude compound was purified by column chromatography (EtOAc / Hexane = 1/3) to give the pure aromatic aldehyde in which the benzyl group was protected [note: two equivalents of K2CO3 were used in the synthesis of compound 18, 2.4 equivalents of benzyl bromide and 4.0 equivalents of K2CO3 was used for the synthesis of Compound 19).
82% With potassium carbonate; potassium iodide In acetone at 20℃; for 4 h; Inert atmosphere A stirred suspension of 3,5-dihydroxybenzaldehyde (690mg, 5mmol), potassium carbonate (3.46g, 25mmol) and potassium iodide (166.0mg, 1mmol) in acetone (15mL) was treated dropwise with benzyl bromide (1.18mL, 10mmol) and stirring continued for 4h at room temperature. The resulting suspension was concentrated under reduced pressure and the crude mass subjected to flash column chromatography (silica, 4:1 v/v hexane/ethyl acetate) and concentration of the relevant fractions (Rf=0.58 in 4:1 v/v hexane/ethyl acetate) afforded the title compound as a white powder (1.3g, 82percent) m.p. 80–81°C. (0031) 1H NMR (DMSO-d6, 500MHz): δ 9.91 (s, 1H), 7.48–7.44 (m, 4H), 7.43–7.38 (m, 4H), 7.37–7.32 (m, 2H), 7.17 (d, J=2.3Hz, 2H), 7.01 (t, J=2.3Hz, 1H), 5.17 (s, 4H) ppm. 13C NMR (DMSO-d6, 126MHz): δ 192.6, 159.9, 138.3, 136.6, 128.4, 127.9, 127.7, 108.2, 108.1, 69.6ppm. IR (diamond cell, neat) νmax: 1686, 1591, 1447, 1381, 1349, 1296, 1170, 1048, 829, 739, 719, 694, 675, 629cm−1. LRMS (+ESI) m/z: 319 [(M+H)+, 100percent]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5438 - 5443
[2] Patent: KR2018/16809, 2018, A, . Location in patent: Paragraph 0104; 0111-0113; 0116; 0124; 0125
[3] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 730 - 740
[4] Tetrahedron, 1994, vol. 50, # 38, p. 11097 - 11112
[5] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648
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Reference: [1] Synthetic Communications, 1999, vol. 29, # 14, p. 2501 - 2506
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