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Chemical Structure| 118-93-4
Chemical Structure| 118-93-4
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Product Details of [ 118-93-4 ]

CAS No. :118-93-4 MDL No. :MFCD00002219
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JECYUBVRTQDVAT-UHFFFAOYSA-N
M.W :136.15 Pubchem ID :8375
Synonyms :
2'-Hydroxyacetophenone

Calculated chemistry of [ 118-93-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.66
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.728 mg/ml ; 0.00535 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 0.641 mg/ml ; 0.00471 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.13
Solubility : 1.02 mg/ml ; 0.00746 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 118-93-4 ]

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 [ 118-93-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 118-93-4 ]
  • Downstream synthetic route of [ 118-93-4 ]

[ 118-93-4 ] Synthesis Path-Upstream   1~43

  • 1
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YieldReaction ConditionsOperation in experiment
50% With sodium hydroxide In benzene STR39 Method C--Option 1 (Method "C-1")
To a stirred mixture of sodium hydride (3.0 equiv., washed free of mineral oil) and diethyl carbonate (10.0 equiv.) in anhydrous benzene was added a solution of compound (3) (1.0 equiv.) in anhydrous benzene, dropwise at room temperature.
The reaction mixture was then refluxed under nitrogen atmosphere overnight, cooled to room temperature, then stirred vigorously with 1N NaOH for 3 hours.
The separated aqueous layer was acidified with 6N HCl, and the precipitated solid was then extracted with ethyl acetate.
The combined organic extracts were washed with water to pH 5-6 for aqueous phase, dried over Na2 SO4 and concentrated to give 4-hydroxycoumarin (4) as an off-white solid (50-87percent).
Reference: [1] Synthetic Communications, 2001, vol. 31, # 8, p. 1195 - 1200
[2] Journal of the American Chemical Society, 2010, vol. 132, # 1, p. 185 - 194
[3] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13985 - 13997
[4] Organic Letters, 2017, vol. 19, # 4, p. 934 - 937
[5] Patent: US5959109, 1999, A,
[6] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 389 - 402
[7] Advanced Synthesis and Catalysis, 2013, vol. 355, # 13, p. 2550 - 2557
[8] Physical Chemistry Chemical Physics, 2013, vol. 15, # 38, p. 15981 - 15994
[9] Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3721 - 3734
[10] Organic Letters, 2014, vol. 16, # 19, p. 5188 - 5191
[11] Tetrahedron, 2014, vol. 70, # 39, p. 6995 - 7005
[12] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1014 - 1018
[13] European Journal of Medicinal Chemistry, 2016, vol. 116, p. 76 - 83
[14] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 10 - 16
[15] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 6, p. 724 - 733
[16] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 828 - 839
[17] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1652 - 1665
[18] Tetrahedron, 2018, vol. 74, # 9, p. 970 - 974
[19] Chinese Chemical Letters, 2016, vol. 27, # 2, p. 287 - 294
[20] New Journal of Chemistry, 2018, vol. 42, # 14, p. 11276 - 11279
[21] Tetrahedron, 1989, vol. 45, p. 6867 - 6874
  • 2
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1982, # 21, p. 1283 - 1284
[2] Tetrahedron, 1985, vol. 41, # 21, p. 4813 - 4820
[3] Tetrahedron, 1985, vol. 41, # 21, p. 4813 - 4820
[4] Synthesis, 1988, # 3, p. 257 - 259
[5] Tetrahedron, 1985, vol. 41, # 21, p. 4813 - 4820
  • 3
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  • [ 1076-38-6 ]
Reference: [1] Synthetic Communications, 2001, vol. 31, # 8, p. 1195 - 1200
  • 4
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  • [ 118-93-4 ]
  • [ 1076-38-6 ]
Reference: [1] Synthetic Communications, 2001, vol. 31, # 8, p. 1195 - 1200
  • 5
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  • [ 1076-38-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 28, p. 4995 - 4998
[2] Australian Journal of Chemistry, 2016, vol. 69, # 1, p. 98 - 106
  • 6
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  • [ 33842-02-3 ]
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 24, p. 6502 - 6508
  • 7
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 24, p. 6502 - 6508
[2] Journal of Organic Chemistry, 1992, vol. 57, # 24, p. 6502 - 6508
  • 8
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Reference: [1] Journal of the Chemical Society, 1948, vol. 2, p. 174 - 176
[2] Patent: US2449162, 1947, ,
[3] Patent: US2449162, 1947, ,
  • 9
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  • [ 105-58-8 ]
  • [ 71-43-2 ]
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Reference: [1] Journal of the Chemical Society, 1948, vol. 2, p. 174 - 176
[2] Patent: US2449162, 1947, ,
[3] Patent: US2449162, 1947, ,
  • 10
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YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 8
4-Oxo4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80° C. for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH=2 with concentrated HCl.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2*).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2*), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCl (110 mL) and heated to 85° C. overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2*125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261° C.; 1H NMR (300 MHz, DMSO-d6) δ8.03 (m, 1H), 7.85 (m, 1H), 7.71 (m, 1H), 7.51 (m, 1H), 6.89 (s, 1H).
83% With hydrogenchloride; sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 19 STR41 4-Oxo-4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80° C. for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH=2 with concentrated hydrochloric acid.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2*).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2*), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCl (110 mL) and heated to 85° C. overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2*125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261° C.; 1 H NMR (DMSO-d6, 300 MHz) δ 8.03 (m, 1 H), 7.85 (m, 1 H), 7.71 (m, 1 H), 7.51 (m, 1 H), 6.89 (s, 1 H).
Reference: [1] Patent: US6469031, 2002, B1,
[2] Patent: US6051586, 2000, A,
[3] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1026,1029; engl. Ausg. S. 1004, 1006
[4] Helvetica Chimica Acta, 1951, vol. 34, p. 767,774
[5] Chimica Therapeutica, 1968, vol. 3, p. 270 - 273
[6] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 582 - 588
  • 11
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YieldReaction ConditionsOperation in experiment
83.5% With hydrogenchloride; sodium ethanolate; sodium In acetic acid-concentrated hydrochloric acid; ethanol; water REFERENCE EXAMPLE 1
2'-hydroxyacetophenone (25.7 g) and diethyl oxalate (33.1 g) were added to a solution of sodium ethoxide in ethanol (prepared from 13.0 g of sodium and 375 ml of ethanol), and the mixture was heated for 1 hour while refluxing.
After the reaction mixture was cooled to room temperature, ethyl ether (500 ml) was added, and the separating crystals were collected by filtration.
To this crystal, 2N hydrochloric acid (600 ml) was added, followed by ethyl ether extraction.
The ethyl ether layer was washed with water and dried (MgSO4), after which it was concentrated under reduced pressure.
The residual oily substance was dissolved in acetic acid-concentrated hydrochloric acid (1:1,200 ml) and heated for 1 hour while refluxing.
The reaction mixture was poured over water (1 liter); the separated crystals were collected by filtration and then washed by sequential additions of water, ethanol and ethyl ether in that order, to yield 4-oxo-4H-1-benzopyran-2-carboxylic acid (83.5percent), which was then recrystallized from ethanol to yield colorless needles having a melting point of 240° to 241° C. (decomposed).
Reference: [1] Patent: US5580863, 1996, A,
  • 12
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YieldReaction ConditionsOperation in experiment
83% With sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 8
4-Oxo-4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80°C for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH = 2 with concentrated HCI.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2x).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2x), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCI (110 mL) and heated to 85°C overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2 x 125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261 °C; 1H NMR (300 MHz, DMSO-d6) δ 8.03 (m, 1 H), 7.85 (m, 1 H), 7.71 (m, 1 H), 7.51 (m, 1 H), 6.89 (s, 1 H).
Reference: [1] Patent: EP1040106, 2002, B1,
  • 13
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
[2] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 911 - 914
  • 14
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  • [ 1139-83-9 ]
  • [ 480-66-0 ]
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
  • 15
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Reference: [1] Patent: US6469031, 2002, B1,
[2] Organic Letters, 2018, vol. 20, # 13, p. 3928 - 3932
  • 16
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Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 431 - 438
  • 17
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  • [ 480-66-0 ]
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
  • 18
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YieldReaction ConditionsOperation in experiment
87% With perchloric acid; C13H9BrN3O4V; dihydrogen peroxide; potassium bromide In water at 20℃; for 0.583333 h; General procedure: In a 50mL round bottom flask equipped with a magnetic stirringbar, 2-hydroxyacetophenone (10 mmol) were added. To this solution,KBr (40 mmol) dissolved in 20 mL water was added and thendissolved by stirring at ambient temperature followed by additionof a 30percent H2O2 (4 mmol). To this reaction mixture, vanadium(V)complex (0.01 mmol) and 70percent HClO4 (4 mmol) were added and thereaction mixture was stirred at 0 C and then after 10 min at roomtemperature. An additional 4 mmol of 70percent HClO4was further addedin three equal portions after every 10 min with continuous stirring.In addition, all the reactions were monitored using thin layerchromatography. The NMR spectra of bromination products aregiven in the supporting information.
72% With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 80℃; General procedure: A modified reaction route: NBS (1.2 equiv.) was added to a solution of appropriately substitutedacetophenones 9a–9l (1.0 equiv.) in CH3CN (15 mL) with p-TSA (0.2 equiv.). The solution washeated at 80 °C for 3-5 h until all the starting materials had been consumed (TLC monitored). Thereaction mass was poured in ice-cold water and extracted with DCM (3 × 20 mL). Anhydrous Na2SO4was added to the combined organic layer, filtered and the excess solvent was removed under reducedpressure. The resultant solid/ liquid obtained were washed with hexane to yield compounds 10a–10i.4,5
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[2] Tetrahedron, 2001, vol. 57, # 11, p. 2203 - 2211
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[4] Synthetic Communications, 2006, vol. 36, # 19, p. 2877 - 2881
[5] Journal of Organometallic Chemistry, 2018, vol. 876, p. 10 - 16
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 408 - 411
[7] Organic Letters, 2015, vol. 17, # 19, p. 4890 - 4893
[8] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 2861 - 2864
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[10] RSC Advances, 2014, vol. 4, # 107, p. 62308 - 62320
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[17] Patent: US6329399, 2001, B1,
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Reference: [1] Journal of the Chemical Society, 1955, p. 18
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  • [ 37924-85-9 ]
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  • [ 24673-56-1 ]
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  • 23
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[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[3] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4
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[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[3] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4
  • 25
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[3] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935
  • 26
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  • 28
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YieldReaction ConditionsOperation in experiment
38% With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation In acetonitrile at 20℃; for 5 h; Inert atmosphere; Irradiation; Green chemistry 1-methyl-3-cyanoquinoline salt as a photosensitizer, Cobalt oxime complex 2 as a cobalt catalyst, 5mL of acetonitrile was added 2.69 mg (1 × 10 -2 mmol) photosensitizer and 2.80 mg (6 × 10 -3 mmol) cobalt catalyst, Replacing the atmosphere with Ar atmosphere And then Add 0.2 mmol of acetophenone (R1 is COCH3, R2, R3, R4 are independently H) and 2 mmo 1 H20.. Room temperature, high pressure mercury lamp irradiation5h. After the reaction was completed, the H2 production was detected by GC (TCD) and the conversion of benzene by GC (FID), And then separated by column. Nuclear magnetic hydrogen Spectrum and mass spectrometry identified the product as 2'- hydroxyacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone. Acetophenone conversion is 58percent, Yields of 2'-hydroxyacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone were 38percent, 6percent and 14percent, respectively The rate is 56percent
Reference: [1] Patent: CN107324975, 2017, A, . Location in patent: Paragraph 0112-0113
[2] Journal of Physical Chemistry A, 1997, vol. 101, # 45, p. 8402 - 8408
[3] Tetrahedron Letters, 2005, vol. 46, # 45, p. 7729 - 7732
[4] Chemical Communications, 2006, # 9, p. 1012 - 1014
[5] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 13995 - 14006
[6] Chinese Journal of Catalysis, 2015, vol. 36, # 7, p. 1086 - 1092
[7] Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10080 - 10083
[8] Catalysis Letters, 2015, vol. 145, # 4, p. 1014 - 1021
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Reference: [1] Chinese Journal of Catalysis, 2012, vol. 33, # 2-3, p. 518 - 522
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YieldReaction ConditionsOperation in experiment
25% With N-Bromosuccinimide; diisopropylamine In carbon disulfide at 0 - 20℃; N-Bromosuccinimide (5.25 g, 29.5 mmol) was added at 0° C. to a mixture of 1-(2-hydroxyphenyl)ethanone (4.00 g, 29.5 mmol) and diisopropylamine (0.42 mL, 2.95 mmol) in carbon disulfide (50 mL), and the mixture was stirred for 1 hour at room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate aqueous solution and water, then dried over magnesium sulfate, filtered, and concentrated at reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane 0:10-->2:8) to give 1.60 g of the titled compound (yield 25percent).
Reference: [1] Patent: US2010/41891, 2010, A1, . Location in patent: Page/Page column 46
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5226 - 5237
[3] Dalton Transactions, 2016, vol. 45, # 7, p. 3055 - 3062
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2753 - 2771
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 36, p. 9418 - 9426
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  • [ 1450-75-5 ]
YieldReaction ConditionsOperation in experiment
61% With Oxone; ammonium bromide In methanol at 20℃; for 4.5 h; General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
  • 35
  • [ 118-93-4 ]
  • [ 22362-66-9 ]
  • [ 1836-05-1 ]
  • [ 1450-75-5 ]
YieldReaction ConditionsOperation in experiment
19 %Chromat. With N-Bromosuccinimide In acetonitrile at 20℃; for 2 h; General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na2S2O3 (10 mL) and extracted with ethyl acetate (70 mL). The organic solution was then washed with additional 10percent Na2S2O3 (2 * 10 mL), followed by deionized water (3 * 15 mL) and brine (2 * 10 mL). The organic solution was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo. The major product of each reaction was isolated by centrifugal thin-layer chromatography using a 2 mm thick silica gel 60GF254 coated plate (5percent CH2Cl2/hexanes). The products reported herein are known compounds and were characterised by GC-MS, IR, 1H and 13C NMR. Their spectroscopic data are in agreement with those reported in the literature.
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
[2] Tetrahedron, 2017, vol. 73, # 46, p. 6564 - 6572
  • 36
  • [ 118-93-4 ]
  • [ 1450-76-6 ]
  • [ 28177-69-7 ]
YieldReaction ConditionsOperation in experiment
80 g With nitric acid In dichloromethane at 40℃; In a four-necked flask, o-hydroxyacetophenone: 175 g, acetic acid: 183 g and methylene chloride: 800 mL were sequentially added, Heating to 40 degrees, slowly dropping 63percent concentrated nitric acid: 165g, control the temperature at 40 degrees, dropping time of 4-6 hours, the end of the drop, 40 degrees for 4-6 hours, the end of the reaction water: 500g stirring 30 minutes, extraction stratification, the organic layer was concentrated 200g crude. To the four-necked flask, 200 g of the above crude product and 900 g of toluene were charged and heated to 60-70 ° C. 70-80 degrees reaction 2-4 hours, cooling to 30-50 degrees, filtration, filter cake drying after adding to the four bottles, add methanol: 100g, water: 800g, heated to 50-60 degrees, slowly drops Add acetic acid: 150g, dropping finished in 60-70 degrees for 2 hours, fell to room temperature filtration, the cake was dry A-2: 80g.
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3353 - 3362
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3353 - 3362
[3] Asian Journal of Chemistry, 2015, vol. 27, # 6, p. 2117 - 2124
[4] Patent: WO2009/85256, 2009, A1, . Location in patent: Page/Page column 55
[5] Patent: CN103980257, 2016, B, . Location in patent: Paragraph 0033; 0034; 0035
  • 37
  • [ 118-93-4 ]
  • [ 28177-69-7 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie, 1963, vol. 18, p. 605 - 612
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3353 - 3362
  • 38
  • [ 118-93-4 ]
  • [ 28177-69-7 ]
  • [ 85-38-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 179
  • 39
  • [ 118-93-4 ]
  • [ 7298-67-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3353 - 3362
  • 40
  • [ 118-93-4 ]
  • [ 50-80-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3353 - 3362
  • 41
  • [ 118-93-4 ]
  • [ 407-25-0 ]
  • [ 151668-40-5 ]
YieldReaction ConditionsOperation in experiment
98% at 80℃; for 3 h; 2-Hydroxyacetophenone (0.01 mol) was dissolved in trifluoroacetic anhydride (0.02 mol) and pyridine (0.01 mol) was added to this dissolution. The reaction mixture was heated at 80 °C and stirred for three hours. After cooling the reaction mixture was treated with 1 M hydrochloric acid (5 ml) and methylene chloride (5 ml) and washed thoroughly with distilled water. The organic layer was dried over sodium sulfate anhydride, the solvent removed in a rotary evaporator and the residue dried in vacuum. If necessary the desired chromone was separated from starting materials through flash chromatography using 10percent ethyl acetate in hexane.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 13, p. 1436 - 1440
[2] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
  • 42
  • [ 118-93-4 ]
  • [ 151668-40-5 ]
Reference: [1] Russian Journal of Organic Chemistry, 1993, vol. 29, # 1.1, p. 74 - 77[2] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 1, p. 89 - 93
[3] Russian Journal of Organic Chemistry, 1993, vol. 29, # 1.1, p. 74 - 77[4] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 1, p. 89 - 93
  • 43
  • [ 118-93-4 ]
  • [ 144707-18-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1094 - 1097
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