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[ CAS No. 22042-73-5 ]

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CAS No. :22042-73-5 MDL No. :MFCD00191450
Formula : C9H10O3 Boiling Point : 335.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :166.17 g/mol Pubchem ID :89178
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22042-73-5 ]

  • Upstream synthesis route of [ 22042-73-5 ]
  • Downstream synthetic route of [ 22042-73-5 ]

[ 22042-73-5 ] Synthesis Path-Upstream   1~3

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  • [ 22042-73-5 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12 h; 250mL round bottom flask was added 10g (82.0mmol) of p-hydroxybenzaldehyde, 30mLDMF dissolved and then was added 22.6g (163.8mmol) of potassium carbonate and 12.3g (98.3mmol) 2- bromoethanol, the reaction at 100 12h; TLC ( V (petroleum ether): V (ethyl acetate) = 5: 1) after the completion of the reaction is determined starting material was cooled to room temperature, the reaction solution was poured into water, and extracted three times with 200mL ethyl acetate, dried over anhydrous sodium sulfate, and concentrated column chromatography (the V (petroleum ether): the V (ethyl acetate) = 10: 1) to give a white product was isolated 11.3g, 83percent yield
83% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12 h; To a solution of 4-hydroxybenzaldehyde (10.0 g, 82.0 mmol) in dry DMF (80 mL), K2CO3 (22.6 g,163.8 mmol) and 2-bromoethanol (12.3 g, 98.3 mmol) were added. The reaction mixture was heatedto 100 °C for 12 h with monitoring by TLC. The resulting solution was extracted with ethyl acetate(3 80 mL) and dried over anhydrous Na2SO4. The solvents of the combined organic layer wereremoved under reduced pressure and the residue was purified by flash chromatography on silica gel(200–300 mesh) using petroleum ether and ethyl acetate (v/v = 8:1) as eluents to afford compound 2as a pale yellow liquid (11.3 g, 83percent). 1H-NMR (300 MHz, CDCl3) δ 9.86 (s, 1H, PhCHO), 7.74–7.90(m, 2H, Ar-H), 6.92–7.10 (m, 2H Ar-H), 4.13–4.20 (m, 2H, PhOCH2), 3.95–4.04 (m, 2H, C H2OH).
81% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2 h; Take 1.22g of 4-hydroxybenzaldehyde and 1.87g of 2-bromoethanol in a 50ml round bottomed flask, add 15ml N, N-dimethylformamide, weighed 2.76g of potassium carbonate was added to the above reaction solution, stirred at 80 2 hours.Themixture wascooled to room temperature,diluted with ethyl acetate and washed with water four times. The organic phase was separated and dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure.The residuewas subjected to silica gel column chromatography using petroleum ether-ethyl acetate = 4: 1, petroleum ether-ethyl acetate = 1: 1 as eluent toobtain 1.35 g of the intermediate A17 as a yellow oily liquid in a yield of 81percent.
80%
Stage #1: With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.166667 h;
Stage #2: for 3 h; Heating / reflux
To a solution of [4-HYDROXYBENZALDEHYDE] (366 mg, 3 [MMOL)] in anhydrous DMF [(7ML),] under nitrogen atmosphere, K2CO3 (829 mg, 6 [MMOL),] and, after 10 minutes, bromoethanol (450 mg, 3.6 [MMOL)] were added. The mixture was heated to reflux for 3 hours, then water was added and the product was extracted with [CH2CI2.] The organic layers were washed with water and with NaCl saturated solution, dried with [NA2SO4.] After evaporation of the solvent, the crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 2/1); 400 mg (yield 80percent) of pure product of the title were obtained. 'H NMR (300 MHz, [DMSO-D6)] : 9.85 (1H, s), 7.84 (2H, d, J = 8.7 Hz), 7.12 (2H, d, J = 8.7 Hz), 4.87 (1H, t, J = 5.1 Hz), 4.10 (2H, dt, J = 5.1 Hz, 4.8 Hz), 3.73 (1H, t, J = 4.8 [HZ).] [13C] NMR (75 MHz, [DMSO-D6)] : 191.7, 164.2, 132.2, 130.0, 115.4, 70.5, 59.8.
70% With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 12 h; To a solution of 4-hydroxybenzaldehyde (1 g,8.19 mmol) in dry DMF (8 mL), K2CO3 (2.26 g, 16.4 mmol) and 2-bromoethanol (2.1 g, 16.4 mmol) were added. The reaction mixture was heated to 55 °C for 12 h.Completion of reaction was observed by TLC (1:9/MeOH:CH2Cl2, Rf 0.60). The reactionmixture was diluted with EtOAc (40 mL), washed successively with H2O (50 mL) and brine (20mL), then dried over MgSO4. The organic layer was removed under reduced pressure and theresidue was purified by flash chromatography (SiO2, 1:9/MeOH:CH2Cl2) to afford compound 23as a viscous colorless liquid (950 mg, 70percent)
63% With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 15 h; To a stirred solution of 4-hydroxybenzaldehyde (40.0 g, 0.327 mol) in dry DMF was added anhydrous potassium carbonate (54.32 g, 0.392 mol), and 2-bromoethanol (49.0 g, 27.8 ml., 0.392 mol) at room temperature and the resulting reaction mixture was heated at 90 0C for 15 h. The reaction mixture was allowed to come to room temperature and then added ice cold water (500 ml) to it. The aqueous layer was saturated with NaCl and extracted with ethyl acetate (5χ60 ml). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated at reduced pressure to get a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 25percent ethyl acetate-hexanes as an eluent to yield the title compound (34.0 g, 63percent). MS: m/z 167 (M+l) 1H NMR (CDCl3, 200 MHz): δ 2.07 (br s, IH), 4.03 (t, J= 4.6 Hz, 2H), 4.17 (t, J= 4.6 Hz, 2H)5 7,04 (d, J= 8.6 Hz, 2H), 7.84 (d, J= 8.6 Hz, 2H), 9.88 (s, IH).
60% With potassium carbonate In 2,4-dichlorophenoxyacetic acid dimethylamine at 20℃; for 72 h; D. 1 Synthesis of (E) 3- 4- (2-hydroxyetoxy) benzylidenel-5, 6- dimethoxy-1, 3-dihydro-indol-2-one.; Step 1 : 4- (2-hydroxyethoxy)-benzaldehyde.; A solution of p-hydroxybenzaldehyde (2 g, 0.016 moles) and K2CO3 (2.72 g, 0. 0197 moles) in DMA (10 ml), kept under strong stirring and at room temperature, was dropwise added with 2-bromoethanol (1.39 ml, 0.0197 moles). After 3 days, the reaction was quenched by addition of 200 ml of H2O and the mixture was extracted with 3x50 ml of Et2O and 2x50 ml of AcOEt. The combined organic phases were dried over Na2SO4 and the solvent was evaporated off to afford an oil which was purified by filtration on silica gel (eluent first with i-Pr2O then with Et2O) thereby obtaining 1.6 g (0.0096 moles, yield 60percent) of a colorless oil. 1H NMR (DMSO-d6) N-3425: 8 3.74 (2H, q), 8 4.11 (2H, t), 8 4.92 (1H, t), 8 7.13 (2H, dd, J=9.5 Hz), 5 7.86 (2H, dd, J=9.5 Hz), 6 9. 87 (1H, s).
60% With potassium carbonate In 2,4-dichlorophenoxyacetic acid dimethylamine at 20℃; for 72 h; Step 1:
4-(2-hydroxyethoxy)-benzaldehyde.
A solution of p-hydroxybenzaldehyde (2 g, 0.016 moles) and K2CO3 (2.72 g, 0.0197 moles) in DMA (10 ml), kept under strong stirring and at room temperature, was dropwise added with 2-bromoethanol (1.39 ml, 0.0197 moles).
After 3 days, the reaction was quenched by addition of 200 ml of H2O and the mixture was extracted with 3*50 ml of Et2O and 2*50 ml of AcOEt.
The combined organic phases were dried over Na2SO4 and the solvent was evaporated off to afford an oil which was purified by filtration on silica gel (eluent first with i-Pr2O then with Et2O) thereby obtaining 1.6 g (0.0096 moles, yield 60percent) of a colorless oil.
1H NMR (DMSO-d6) N-3425: δ 3.74 (2H, q), δ 4.11 (2H, t), δ 4.92 (1H, t), δ 7.13 (2H, dd, J=9.5 Hz), δ 7.86 (2H, dd, J=9.5 Hz), δ 9.87 (1H, s).

Reference: [1] Patent: CN105503712, 2016, A, . Location in patent: Paragraph 0031; 0032; 0033
[2] Molecules, 2017, vol. 22, # 6,
[3] Patent: CN107286098, 2017, A, . Location in patent: Paragraph 0174-0177
[4] Patent: WO2004/35590, 2004, A2, . Location in patent: Page 22-23
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3680 - 3686
[6] Australian Journal of Chemistry, 2013, vol. 66, # 12, p. 1576 - 1583
[7] Patent: WO2008/10238, 2008, A2, . Location in patent: Page/Page column 92
[8] Chemical Communications, 2010, vol. 46, # 45, p. 8651 - 8653
[9] Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 956 - 959
[10] Patent: WO2005/68424, 2005, A1, . Location in patent: Page/Page column 31-32
[11] Patent: US2005/209195, 2005, A1, . Location in patent: Page/Page column 15
[12] Biomacromolecules, 2017, vol. 18, # 8, p. 2594 - 2609
[13] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 65 - 72
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YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In dimethyl sulfoxide for 6 h; Reflux General procedure: A mixture of 4-hydroxybenzaldehyde derivatives (1 mmol), 3-chloropropanol or 2-chloroethanol (1 mmol) and potassium carbonate(3 mmol) in dimethylsulfoxide was refluxed for 6 h. Aftercompletion of reaction which monitored by thin-layer chromatography(TLC), the reaction mixture was diluted with water andextracted with dichloromethan. The solvent was removed underreduced pressure and the residue was purified through columnchromatography. 4.3.1. 4-(2-hydroxyethoxy)benzaldehyde(3m)Yellow oil (80percent); 1H NMR (400 MHz, CDCl3): δ 3.03 (1H, s, OH),3.98 (2H, t, J =4.4 Hz, -CH2-), 4.14 (2H, t, J = 4.4 Hz, -OCH2), 6.98(2H, d, J = 8.4 Hz, Ar-H), 7.80 (2H, d, J= 8.4 Hz, Ar-H), 9.84 (1H, s,CHO) ppm.
73% With potassium carbonate In ethanol at 70℃; for 16 h; Example 20. Preparation of 2-[4-(2-hydroxy-ethoxy)-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0239] To a flask (250 mL) with a magnetic stirrer were added 4-hydroxybenzalde (10.0 g, 81.8 mmol), 2-chloroethanol (26.3 g, 327 mmol), potassium carbonate (22.6 g, 163 mmol), and ethanol (80 mL). The reaction mixture was stirred at 700C for 16 hours. Potassium carbonate was filtered and ethanol was removed. The residue was diluted with ethyl acetate (200 ml_) and washed with 5percent sodium hydroxide (100 ml_), water (100 ml_), and brine (100 ml_). The crude product was purified by column chromatography (silica gel, 230-400 mesh), using hexane / ethyl acetate (1 :1) as eluent, to afford 4-(2-hydroxy-ethoxy)-benzaldehyde. Yield: 10.0 g (73percent).[0240] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.400 g, 2.00 mmol) and 4-(2-hydroxy-ethoxy)-benzaldehyde (0.340 g, 2.00 mmol) in N, N- dimethylacetamide (8 ml_) were added NaHSO3 (0.390 g, 2.20 mmol) and p-TSA (38 mg, 0.20 mmol). The reaction mixture was stirred at 115-1200C for 5 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was diluted with water (40 ml_) and the solid was collected, mixed with methanol (50 ml_), and stirred for 30 min. The solid was filtered and rinsed with ether (30 ml_) to give the title compound as white solid. Yield: 0.42 g (61percent). 1H NMR (400 Hz, DMSO-d6): δ 11.98 (s, 1H), 8.18 (d, 2H), 7.08 (d, 2H), 6.78 (s, 1 H), 6.52 (s, 1H), 4.98 (s, 1 H), 4.10 (t, 2H), 3.90 (s, 3H), 3.84 (s, 3H)1 3.74 (t, 2H). MS (ES+) m/z: 343.13 (M+1).
73% With potassium carbonate In ethanol at 70℃; for 16 h; To a flask (250 mL) with a magnetic stirrer were added 4-hydroxybenzalde (10.0 g, 81.8 mmol), 2-chloroethanol (26.3 g, 327 mmol), potassium carbonate (22.6 g, 163 mmol), and ethanol (80 mL). The reaction mixture was stirred at 70° C. for 16 hours. Potassium carbonate was filtered and ethanol was removed. The residue was diluted with ethyl acetate (200 mL) and washed with 5percent sodium hydroxide (100 mL), water (100 mL), and brine (100 mL). The crude product was purified by column chromatography (silica gel, 230-400 mesh), using hexane/ethyl acetate (1:1) as eluent, to afford 4-(2-hydroxy-ethoxy)-benzaldehyde. Yield: 10.0 g (73percent)
54% With sodium hydroxide In water; butan-1-olReflux 4-Hydroxybenzaldehyde 3 (12.2 g, 0.1 mmol) and 4.4 g of NaOH (0.11 mmol) were dissolved in a mixture of 200 ml of n-BuOH and 30 ml of water. This solution was brought to reflux and a solution of 24.1 ml of 2-chloroethanol (0.3 mmol) in 50 ml of n-BuOH was added over a period of 90 min. The reaction mixture was refluxed overnight. The solvent was evaporated in vacuo, and the residue was purified by silica gel dry flash chromatography (Petroleum ether/EtOAc manual gradient from 0percent to 100percent EtOAc) to afford compound 4 (9.0g, 54percent) as a colourless oil, which solidified upon standing overnight. 1H NMR (400 MHz, CDCl3) δ 9.83 (s, 1H), 7.78 (d, 2H, J=8 Hz), 6.96 (d, 2H, J=8 Hz), 4.11 (t, 2H, J=4 Hz), 3.94 (t, 2H, J=4 Hz), 1.87 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ 190.8, 163.6, 132.0, 130.3, 114.8, 69.5, 61.2.
14.9 g With potassium carbonate In acetonitrile for 8 h; Reflux To a 250 mL three-necked flask equipped with 150 mL of acetonitrile,12.2 g (0.1 mol) of p-hydroxybenzaldehyde and 6.9 g of potassium carbonate (5 mmol) were added,After stirring evenly,Further, 9.66 g (0.72 mol) of chloroethanol was added,Electromagnetic stirring,Heated to reflux for 8 hours,TLC detection to complete disappearance of raw materials,Stop the reaction.Cooled to room temperature,Separate the organic layer,The organic layer was washed with sodium hydroxide solution until no p-hydroxybenzaldehyde was present,Separate the organic layer,Dried over magnesium sulfate,filter,Concentrate the filtrate,To give 14.9 g of compound 1.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6519 - 6522
[2] Journal of the American Chemical Society, 2008, vol. 130, # 50, p. 16996 - 17003
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4235 - 4243
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 639 - 646
[5] Journal of Organometallic Chemistry, 2018, vol. 870, p. 38 - 50
[6] Patent: WO2010/123975, 2010, A1, . Location in patent: Page/Page column 87-88
[7] Patent: US2013/281398, 2013, A1, . Location in patent: Paragraph 0452; 0453
[8] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 12, p. 1634 - 1637
[9] Tetrahedron Letters, 1997, vol. 38, # 11, p. 1907 - 1910
[10] Helvetica Chimica Acta, 1994, vol. 77, # 1, p. 59 - 69
[11] Tetrahedron, 2011, vol. 67, # 31, p. 5572 - 5576
[12] Journal of the American Chemical Society, 1951, vol. 73, p. 906,908
[13] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 752 - 754
[14] Patent: US6353011, 2002, B1, . Location in patent: Figure 3
[15] Patent: CN107163072, 2017, A, . Location in patent: Paragraph 0036; 0037; 0038; 0039; 0046-0049; 0055-0058
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Reference: [1] Green Chemistry, 2017, vol. 19, # 18, p. 4299 - 4304
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