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[ CAS No. 24677-78-9 ]

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CAS No. :24677-78-9 MDL No. :MFCD00003324
Formula : C7H6O3 Boiling Point : 240°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :138.12 g/mol Pubchem ID :90579
Synonyms :

Safety of [ 24677-78-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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  • Upstream synthesis route of [ 24677-78-9 ]
  • Downstream synthetic route of [ 24677-78-9 ]

[ 24677-78-9 ] Synthesis Path-Upstream   1~29

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Reference: [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
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  • [ 769-30-2 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 803 - 807
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  • [ 5768-39-8 ]
Reference: [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
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Reference: [1] Patent: WO2013/153535, 2013, A1,
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  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In acetone at 20℃; for 12 h; General procedure: Anhydrous potassium carbonate (2 g) and ethyl iodide (0.5 ml) were added to 2,4-dihydroxy benzaldehyde (0.7 g, 5 mmol) acetone (30 ml) and the contents stirred for 12 h at room temperature. After the completion of the reaction as indicated by TLC, the mixture concentrated in vacuo and re-dissolved in benzene (3 × 10 ml). The organic layer concentrated and the residue chromatography on silica gel (60–120 mesh) using n-hexane: ethyl acetate mixture (46:4) as eluent to give JA-2 a crystallized solid (0.75 g, 45percent) 2.2.1.7
Preparation of 2-hydroxy-3-methoxybenzaldehyde
The title compound was prepared from 2,3-dihydroxy benzaldehyde (1.0 g, >7 mmol) and methyl iodide (0.5 ml, 7 mmol) by the method as described for 2-hydroxy-4-ethoxy-benzaldehyde to furnish a semisolid (0.48 g, 46percent) analyzed for C8H8O3. IR (KBr Pellet): 3184, 2932, 1668, 1634, 1578, 1498, 1454, 1428, 1374, 1336, 1292, 1260, 1216, 1170, 1114, 998, 926 cm-1. 1H NMR (200 MHz, CDCl3): δ3.87 (3H, s, OMe), 6.92(1H, dd, J = 7.92 & 7.88 Hz, Ar-H), 7.08(1H, d, J = 7.92 Hz, Ar-H),7.14 (1H, d, J = 7.83 Hz, Ar-H),9.87(1H, s, Ar-CHO), 11.07(1H, s, OH). MS M+ m/z (percent) 152(18), 137(8), 121(15), 81(8), 53(100).
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 209 - 219
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1983, # 7, p. 400 - 401
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  • [ 91-10-1 ]
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  • [ 148-53-8 ]
  • [ 95-48-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
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  • [ 100-39-0 ]
  • [ 52085-14-0 ]
Reference: [1] Patent: CN105777632, 2016, A, . Location in patent: Paragraph 0318; 0319; 0320
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  • [ 67984-81-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 11, p. 1552 - 1553
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YieldReaction ConditionsOperation in experiment
87% With aluminum (III) chloride; sodium iodide In acetonitrile at 80℃; for 18 h; Add acetonitrile (40ml) to a 100ml eggplant bottle,Aluminum trichloride (0.752g, 5.64mmol, 1.1eq),NaI (2.305 g, 15.38 mmol, 3.0 eq) and o-vanillin (0.780 g, 5.13 mmol),Heat to 80 ° C, stop stirring after 18 hours of reaction.After cooling to room temperature, it was acidified with 2 mol/L of dilute hydrochloric acid (10 ml), and extracted with ethyl acetate (50 ml × 3). The organic phase was combined and washed with saturated aqueous sodium thiosulfate (10 ml). Washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated, evaporated. )purification,0.620 g of 2,3-dimethoxybenzaldehyde were obtained (yellow solid, yield 87percent).
86.5% With boron tribromide In dichloromethane at 20℃; for 15.5 h; Cooling with ice To a 500 ml three-necked flask was added 30.0 g of o-vanillin, 150 mL of dichloromethane, and placed in an ice bath.53.8 g of boron tribromide was dissolved in 20 mL of dichloromethane and added dropwise for 30 minutes. After the drop is finished, it rises to room temperature.Stirring was continued for 15 h. After adding 50 mL of water, stirring was continued for 1 hour, and the organic phase was separated and concentrated under reduced pressure.24.0 g of 2,3-dihydroxybenzaldehyde was obtained in a yield of 86.5percent and a content of 98.0percent.
85%
Stage #1: With sodium hydroxide In water for 0.5 h;
Stage #2: With dihydrogen peroxide In water at 60℃; for 24 h;
In 2L of four flasks add 121.0g (0.80 µM) (1.0eq) 3 - methoxy -2 - hydroxy benzaldehyde, then in 0.5h dropping in 25percent NaOH aqueous solution of 128g (0.80 µM) (1.0eq), then in 6h in extra drop of 10percent of the 940 ml (3.5eq) of H2O2, Dropped control temperature not exceeding 50 °C, after finishing dripping heating to 60 °C, thermal insulation reflux 18h. After the reaction by adding 10percent hydrochloric acid is acidified to pH=1 - 2, standing, dichloromethane is used for extraction, separating out the lower organic phase, desolution removing dichloromethane, distillation collection 115 - 120 °C/15mmHg fraction, after cooling to obtain the 84.2g yellow solid, namely 2, 3 - dihydroxy benzaldehyde, yield is 85percent, mp=104 - 105 °C.
77.7% With boron tribromide In dichloromethane at -78 - 20℃; for 1 h; Inert atmosphere 10 g (65.7 mmol) of o-vanillin was dissolved in 100 ml of anhydrous dichloromethane under a nitrogen atmosphere at minus 78 ° C.6.3 ml (65.7 mmol) of boron tribromide was added dropwise, and the reaction system was allowed to react at room temperature for one hour.After the reaction is completed, the solution is quenched by dropwise addition of a saturated ammonium chloride solution, and water is added to the reaction system.It was extracted three times with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate.Filter, concentrate, and separate the residue by column chromatography (ethyl acetate/petroleum ether=1:5),9.08 g of the title compound was obtained as a white solid with a yield of 77.7percent.
67% With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18 h; Add aluminum triiodide (2·240 g, 5 · 5 mmol), acetonitrile (40 ml) and DMSO (0.430 g, 5.5 mmol) to a 100 ml eggplant-shaped flask, and heat to 80 ° C with stirring, and stir for 0.5 hour. Then, o-vanillin (0.380 g, 2.5 mmol) was added, and the reaction was further stirred (80 ° C). After the reaction for 18 hours, the stirring was stopped. After cooling to room temperature, 2 mol/L of dilute hydrochloric acid (10 ml) was added to the eggplant-shaped flask. The mixture was extracted with EtOAc (EtOAc (EtOAc)EtOAc. Evaporate to dryness on a rotary evaporator, and the residue was purified by flash column chromatography (ethyl acetate / petroleum ether = 1:4, volume ratio) to give 0.232 g of 2,3-dihydroxybenzaldehyde (yellow solid, The rate is 67percent).
65% With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 8 h; General procedure: To a suspension of AlI3 (5.5 mmol, 1.1 equiv) in hot CH3CN (40 mL) were added sequentially DIC (0.379 g, 3 mmol, 0.6 equiv) and eugenol (1, 0.821 g, 5.0 mmol). The mixture was stirred for 18 h at 80 °C, and then it was cooled to r.t., acidified with HCl (2 mol/L, 10 mL), and extracted with EtOAc (3 × 50 mL). The organic phases were combined, washed with sat. aq Na2S2O3 (10 mL) and brine (10 mL), and was dried (MgSO4). The solvent was removed on a rotary evaporator and the residue was purified by flash column chromatography (PE/EtOAc, 4:1) to afford 2 (0.750 g, 99percent) as a white solid
65% With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 8 h; To a 100 ml eggplant flask were added aluminum triiodide (2.253 g), acetonitrile (40 ml) DIC (0.383 g) and o-vanillin (0. 763 g) were heated to 80 ° C and reacted for 8 hours to stop stirring, After cooling to room temperature, add 2 mol / L dilute hydrochloric acid (10 ml) to the eggplant flask, And extracted with ethyl acetate (50 ml X). The combined organic phases were washed first with a saturated aqueous solution of sodium thiosulfate (10 ml), washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated Instrument evaporated, The residue was purified by flash column chromatography (eluent: ethyl acetate / petroleum ether = 1: 3, volume ratio) To give 0.450 g of 2,3-dihydroxybenzaldehyde (yellow solid in 65percent yield)
37% With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18 h; To a 100 ml eggplant flask was added aluminum triiodide (2.242 g, 5.5 mmol), acetonitrile (40 ml),CaO (0.420 g, 7.5 mmol) and o-vanillin (0.763 g, 5 mmol), heated to 80 °C,After 18 hours of reaction, stirring was stopped. After cooling to room temperature, 2 mol/L dilute hydrochloric acid (10 ml) was acidified in an eggplant-shaped flask.Extract with ethyl acetate (50ml x 3) and combine the organic phases and wash first with saturated aqueous sodium thiosulfate (10ml).It was washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness on a rotary evaporator.The residue was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether=1:3, volume ratio).0.259 g of 2,3-dihydroxybenzaldehyde was obtained (yellow solid, yield 37percent).

Reference: [1] Patent: CN108821955, 2018, A, . Location in patent: Paragraph 0021; 0022; 0025; 0026
[2] Patent: CN108178753, 2018, A, . Location in patent: Paragraph 0023-0025
[3] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13808 - 13809
[4] Patent: CN106699722, 2017, A, . Location in patent: Paragraph 0050-0052
[5] Patent: CN107840845, 2018, A, . Location in patent: Paragraph 0179; 0180; 0181; 0182
[6] Patent: CN108821930, 2018, A, . Location in patent: Paragraph 0150-0152
[7] Synthesis (Germany), 2017, vol. 49, # 12, p. 2721 - 2726
[8] Patent: CN106866377, 2017, A, . Location in patent: Paragraph 0172; 0173
[9] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 3, p. 392 - 397
[10] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
[11] Tetrahedron, 1984, vol. 40, # 13, p. 2529 - 2535
[12] Patent: CN107473916, 2017, A, . Location in patent: Paragraph 0100-0102
[13] Chemische Berichte, 1910, vol. 43, p. 1813
[14] Justus Liebigs Annalen der Chemie, 1911, vol. 383, p. 315
[15] Biochemische Zeitschrift, 1920, vol. 108, p. 90[16] Angewandte Chemie, 1920, vol. 33, p. 137
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Reference: [1] Patent: US6331555, 2001, B1,
[2] Patent: US5990141, 1999, A,
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  • [ 120-80-9 ]
  • [ 68-12-2 ]
  • [ 24677-78-9 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 41, # 1, p. 372 - 376
[2] Journal of the Indian Chemical Society, 2008, vol. 85, # 9, p. 959 - 961
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  • [ 86-51-1 ]
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Reference: [1] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1119 - 1128
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 8, p. 2140 - 2144
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  • [ 50-00-0 ]
  • [ 120-80-9 ]
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Reference: [1] New Journal of Chemistry, 2018, vol. 42, # 6, p. 4590 - 4595
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  • [ 66495-88-3 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 24, p. 9139 - 9144
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  • [ 139-85-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
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  • [ 90087-77-7 ]
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Reference: [1] Organic letters, 2001, vol. 3, # 9, p. 1399 - 1401
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Reference: [1] Organic letters, 2001, vol. 3, # 9, p. 1399 - 1401
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Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 15, p. 1577 - 1580
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Reference: [1] Tetrahedron, 1974, vol. 30, p. 3969 - 3980
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  • [ 35942-09-7 ]
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  • [ 19322-27-1 ]
  • [ 1197-09-7 ]
  • [ 24677-78-9 ]
  • [ 120-80-9 ]
  • [ 488-17-5 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2018,
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  • [ 90-02-8 ]
  • [ 24677-78-9 ]
  • [ 95-01-2 ]
Reference: [1] Patent: DE155731, , ,
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  • [ 91-10-1 ]
  • [ 934-00-9 ]
  • [ 24677-78-9 ]
  • [ 148-53-8 ]
  • [ 95-48-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
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  • [ 90-05-1 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
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  • [ 148-53-8 ]
  • [ 64-19-7 ]
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Reference: [1] Chemische Berichte, 1910, vol. 43, p. 1813
[2] Justus Liebigs Annalen der Chemie, 1911, vol. 383, p. 315
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  • [ 64419-24-5 ]
YieldReaction ConditionsOperation in experiment
59% for 8 h; Reflux In an acetic acid (10 mL) solvent, a solution including 2,3-dihydroxybenzaldehyde (3.0 g, 21.7 mmol), sodium acetate (NaOAc) (3.54 g, 43.4 mmol), and nitroethane (3.24 g, 43.4 mmol) was refluxed for 8 hours.
After cooling, the reaction mixture was distributed between ethyl acetate and water.
Until a pH of the residual aqueous layer reached 8, an organic layer was washed with a saturated NaHCO3 solution.
The organic layer was evaporated, the residual was purified by silica gel column chromatography using hexane and ethyl acetate (2:1) as a developer to obtain Compound 101a (1.88 g, 59percent).
A melting point of 183 to 186° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.76 (br s, 1H), 10.33 (br s, 1H), 7.33 (d, 1H, J=8.4 Hz), 6.38 (d, 1H, J=2.0 Hz), 6.28 (dd, 1H, J=2.0, 8.4 Hz).
Reference: [1] Patent: US2014/37564, 2014, A1, . Location in patent: Paragraph 0293-0295
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  • [ 106-93-4 ]
  • [ 274910-19-9 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: With caesium carbonate In DMF (N,N-dimethyl-formamide) for 2 h; Heating / reflux
Stage #2: With sodium tetrahydroborate In DMF (N,N-dimethyl-formamide); ethanol at 20℃; for 1 h;
Preparation 87; (2,3-Dihydrobenzo [1, 4] dioxin-5-yl) acetonitrile; (2, 3-Dihydrobenzorl, 41dioxin-5-yl) methanol; Dissolve 2,3-Dihydroxybenzaldehyde (25 g, 181 mmol) and 1,2-dibromoethane (34 g, 181 mmol) in N, N-dimethylformamide (500 mL). Add cesium carbonate (118 g, 362 mmol), stir and reflux under nitrogen for 2 hours. Cool the reaction to 20°C, dilute with absolute ethanol (250 mL) and add sodium borohydride (6.8 g, 181 mmol). Stir at 20°C for 1 hour and concentrate under high vacuum to remove the ethanol and dimethylformamide. Dilute the residue with diethyl ether and wash with distilled water, 0.25 molar aqueous sodium hydroxide, and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from 75percent hexane, 25percent ethyl acetate to 25percent hexane, 75percent ethyl acetate to obtain the title compound as a white solid. HRMS : 166.0621 (M); Preparation 129; 2- (2, 3-Dihydrobenzo [1, 4] dioxin-5-yl) acetamide; (2, 3-Dihydrobenzo f 1, 41 dioxin-5-yl) methanol; Dissolve 2,3-dihydroxybenzaldehyde (25 g, 181 mmol) and 1,2-dibromoethane (34 g, 181 mmol) in N, N-dimethylformamide (500 mL). Add cesium carbonate (118 g, 362 mmol), stir and reflux under nitrogen for 2 hours. Cool the reaction to 20°C, dilute with absolute ethanol (250 mL) and add sodium borohydride (6.8 g, 181 mmol). Stir at 20°C for 1 hour and concentrate under high vacuum to remove the ethanol and dimethylformamide. Dilute the residue with diethyl ether and wash with distilled water, 0.25 molar aqueous sodium hydroxide, and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from 75percent hexane, 25percent ethyl acetate to 25percent hexane, 75percent ethyl acetate to obtain 8. 1 g (27percent) of the desired compound as a white solid. HRMS: m/z = 166.0621 (M)
Reference: [1] Patent: WO2003/76442, 2003, A1, . Location in patent: Page/Page column 49; 63-64
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 803 - 807
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