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CAS No. :1450-74-4 MDL No. :MFCD00067788
Formula : C8H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XTGCUDZCCIRWHL-UHFFFAOYSA-N
M.W : 170.59 Pubchem ID :74061
Synonyms :
Chemical Name :1-(5-Chloro-2-hydroxyphenyl)ethanone

Safety of [ 1450-74-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 1450-74-4 ]

* 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 [ 1450-74-4 ]
  • Downstream synthetic route of [ 1450-74-4 ]

[ 1450-74-4 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 1450-74-4 ]
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8657 - 8667
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  • [ 37674-72-9 ]
Reference: [1] Synthesis, 1989, # 9, p. 709 - 710
  • 3
  • [ 876-27-7 ]
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YieldReaction ConditionsOperation in experiment
90% With aluminum (III) chloride In neat (no solvent) at 140 - 150℃; p-Chlorophenyl acetate 2c (10 gm, 0.091mol) was in 500 mL round bottom flask containing aluminium chloride (14.56 gm, 0.11 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compound. The obtained crude compound 3c was recrystallized using aq. ethanol. Yield 90percent. M.p. 54-56 °C.
87% at 0 - 20℃; for 16 h; General procedure: O-Acyloxy benzenes (0.28 mmol) were dissolved in TfOH (3 ml) at 0 °C. The reaction mixture was warmed to room temperature for appropriate time in Table 3, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO3, and saturated NaCl, and dried over MgSO4, then filtrated. The filtrate was concentrated and the residue was subjected silica column chromatography to afford acylated products. All spectral data were identical with the literatures.26
60% at 120 - 160℃; 4-chlorophenyl acetate (2) (0.1 mole) and anhydrous aluminum trichloride (0.11 mole) were mixed thoroughly in a round bottom flask. The reaction mixture was heated gradually at 120°C till HCl gas was completely exhausted. The heating was extended for 2 hours at 160°C. The progress and completion of the reaction was monitored by TLC. At the end of the reaction the resulting aluminum complex was decomposed from crushed ice containing little amount of hydrochloric acid. The crude product was filtered dried and crystallized from methanol. Yield 60percent, m. p. 53-55 °C (Reported m.p. 53°C).
Reference: [1] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[2] Synthesis, 1985, # 9, p. 901 - 902
[3] Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185
[5] Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 151 - 156
[6] Synthesis, 2004, # 11, p. 1789 - 1792
[7] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 5, p. 323 - 329
[8] Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 537 - 548
[9] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2547 - 2549
[10] Journal of Chemical Research, Miniprint, 1989, # 11, p. 2713 - 2739
[11] Chemische Berichte, 1924, vol. 57, p. 92[12] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
[13] Chemische Berichte, 1924, vol. 57, p. 1273
[14] Journal of the Indian Chemical Society, 1949, vol. 26, p. 366,367
[15] Chemische Berichte, 1954, vol. 87, p. 194,201
[16] Monatshefte fuer Chemie, 1965, vol. 96, p. 1214 - 1223
[17] Journal of Medicinal Chemistry, 1971, vol. 14, p. 758 - 766
[18] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1981, vol. 37, # 3, p. 199 - 204
[19] Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 614 - 621
[20] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1366 - 1370
[21] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 21, p. 5996 - 6001
[22] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2007, vol. 46, # 9, p. 1440 - 1444
[23] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6322 - 6328
[24] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 158 - 169
[25] Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4616 - 4620
[26] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062
[27] Russian Journal of Organic Chemistry, 2012, vol. 48, # 5, p. 728 - 735
[28] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2826 - 2831
[29] Bulletin of the Chemical Society of Ethiopia, 2013, vol. 27, # 1, p. 85 - 94
[30] MedChemComm, 2013, vol. 4, # 9, p. 1257 - 1266
[31] Journal of Fluorine Chemistry, 2014, vol. 160, p. 77 - 81
[32] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73
[33] Medicinal Chemistry Research, 2015, vol. 24, # 7, p. 3008 - 3020
[34] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 329, p. 238 - 245
[35] Heterocyclic Communications, 2017, vol. 23, # 4, p. 325 - 330
[36] Heterocyclic Communications, 2018, vol. 24, # 1, p. 59 - 65
  • 4
  • [ 186956-36-5 ]
  • [ 1450-74-4 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; General procedure: A mixture of allyl phenyl ethers 1 (1 mmol) and iodine (20 molpercent) in polyethylene glycol-400(10 mL) was stirred at room temperature for 25-30 minutes. The reaction mixture was poured incold solution of sodium thiosulphate and extracted by ethyl acetate. The combine organic layerwas dried over anhydrous Na2SO4 and evaporated under vacuum and purified by columnchromatography. The corresponding product was obtained in 86-96percent yield.
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 929 - 935
  • 5
  • [ 99-02-5 ]
  • [ 1450-74-4 ]
  • [ 3226-34-4 ]
YieldReaction ConditionsOperation in experiment
6% 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 added2.69 mg (1 × 10 -2 mmol) of photosensitizer and 2.80 mg (6 × 10 -3 mmol) of cobalt catalyst were charged, the atmosphere was replaced with Ar atmosphere, and then0.2 mmol of 3'-chloroacetophenone (R1 is COCH3, R3 is Cl, R2, R4 are independently H) and 2 mmol of H2O are added. Room temperature, high pressureMercury lamp irradiation 5h. After the reaction was completed, the H2 production was detected by GC (TCD) and the conversion of benzene by GC (FID), Then over the column points. Nuclear magnetic resonance spectroscopy and mass spectrometry identification of broad-based as 3 '- chloro -2_ hydroxyacetophenone, 3' - chloro -4_ light base acetophenone and 3 '- chloro-6_Hydroxyacetophenone.The conversion of 3'-chloroacetophenone was 43percent. The conversion of 3'-chloro-2-hydroxyacetophenone, 3'-chloro-4-hydroxyacetophenone and 3'-chloro-6-hydroxyacetophenone The yields were 6percent, 2percent and 34percent respectively, and the H2 yield was 42percent.
Reference: [1] Patent: CN107324975, 2017, A, . Location in patent: Paragraph 0126-0127
  • 6
  • [ 118-93-4 ]
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Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
[2] Tetrahedron Letters, 2017, vol. 58, # 10, p. 985 - 990
[3] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935
  • 7
  • [ 106-48-9 ]
  • [ 75-36-5 ]
  • [ 1450-74-4 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 1, p. 67 - 74
[2] Chemische Berichte, 1897, vol. 30, p. 1771
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 9, p. 2108 - 2116
  • 8
  • [ 75632-99-4 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 695 - 698
  • 9
  • [ 87974-51-4 ]
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Reference: [1] Synthetic Communications, 2000, vol. 30, # 8, p. 1521 - 1527
  • 10
  • [ 106-48-9 ]
  • [ 1450-74-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1366 - 1370
[2] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 5, p. 323 - 329
[3] Chemische Berichte, 1954, vol. 87, p. 194,201
[4] Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649
[5] Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4616 - 4620
[6] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2826 - 2831
[8] Bulletin of the Chemical Society of Ethiopia, 2013, vol. 27, # 1, p. 85 - 94
[9] Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 151 - 156
[10] MedChemComm, 2013, vol. 4, # 9, p. 1257 - 1266
[11] Journal of Fluorine Chemistry, 2014, vol. 160, p. 77 - 81
[12] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73
[13] Medicinal Chemistry Research, 2015, vol. 24, # 7, p. 3008 - 3020
[14] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[15] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 329, p. 238 - 245
[16] Heterocyclic Communications, 2017, vol. 23, # 4, p. 325 - 330
[17] Heterocyclic Communications, 2018, vol. 24, # 1, p. 59 - 65
  • 11
  • [ 876-27-7 ]
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Reference: [1] Patent: US2003/176482, 2003, A1,
  • 12
  • [ 6342-64-9 ]
  • [ 1450-74-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 619 - 622
  • 13
  • [ 118-93-4 ]
  • [ 1450-74-4 ]
  • [ 3321-92-4 ]
  • [ 3226-34-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813
  • 14
  • [ 51085-92-8 ]
  • [ 33533-99-2 ]
  • [ 1450-74-4 ]
  • [ 91998-75-3 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 2, p. 166 - 172
  • 15
  • [ 64-19-7 ]
  • [ 106-48-9 ]
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Reference: [1] Chemische Berichte, 1954, vol. 87, p. 194,201
[2] Chemische Berichte, 1954, vol. 87, p. 194,201
  • 16
  • [ 55877-79-7 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 619 - 622
  • 17
  • [ 118-93-4 ]
  • [ 1450-74-4 ]
  • [ 3321-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
  • 18
  • [ 623-12-1 ]
  • [ 75-36-5 ]
  • [ 1450-74-4 ]
  • [ 6342-64-9 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 92[2] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
  • 19
  • [ 159214-70-7 ]
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Reference: [1] Chemische Berichte, 1927, vol. 60, p. 946
  • 20
  • [ 7446-70-0 ]
  • [ 876-27-7 ]
  • [ 1450-74-4 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 92[2] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
[3] W., vol. 57, p. 1275
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  • [ 7446-70-0 ]
  • [ 876-27-7 ]
  • [ 108-88-3 ]
  • [ 1450-74-4 ]
  • [ 122-00-9 ]
Reference: [1] Rikagaku Kenkyusho Iho, 1943, vol. 22, p. 828,830, 831[2] Chem.Abstr., 1949, p. 7924
[3] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1943, vol. 41, p. 182,188[4] Rikagaku Kenkyusho Iho, 1942, vol. 21, p. 247,249, 251
  • 22
  • [ 75-15-0 ]
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Reference: [1] Chemische Berichte, 1924, vol. 57, p. 92[2] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
  • 23
  • [ 99-02-5 ]
  • [ 1450-74-4 ]
  • [ 3226-34-4 ]
YieldReaction ConditionsOperation in experiment
6% 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 added2.69 mg (1 × 10 -2 mmol) of photosensitizer and 2.80 mg (6 × 10 -3 mmol) of cobalt catalyst were charged, the atmosphere was replaced with Ar atmosphere, and then0.2 mmol of 3'-chloroacetophenone (R1 is COCH3, R3 is Cl, R2, R4 are independently H) and 2 mmol of H2O are added. Room temperature, high pressureMercury lamp irradiation 5h. After the reaction was completed, the H2 production was detected by GC (TCD) and the conversion of benzene by GC (FID), Then over the column points. Nuclear magnetic resonance spectroscopy and mass spectrometry identification of broad-based as 3 '- chloro -2_ hydroxyacetophenone, 3' - chloro -4_ light base acetophenone and 3 '- chloro-6_Hydroxyacetophenone.The conversion of 3'-chloroacetophenone was 43percent. The conversion of 3'-chloro-2-hydroxyacetophenone, 3'-chloro-4-hydroxyacetophenone and 3'-chloro-6-hydroxyacetophenone The yields were 6percent, 2percent and 34percent respectively, and the H2 yield was 42percent.
Reference: [1] Patent: CN107324975, 2017, A, . Location in patent: Paragraph 0126-0127
  • 24
  • [ 118-93-4 ]
  • [ 1450-74-4 ]
  • [ 3321-92-4 ]
  • [ 3226-34-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813
  • 25
  • [ 1450-74-4 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020
  • 26
  • [ 1450-74-4 ]
  • [ 111841-05-5 ]
Reference: [1] Patent: WO2016/16370, 2016, A1,
  • 27
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  • [ 133406-29-8 ]
Reference: [1] Russian Chemical Bulletin, 2000, vol. 49, # 3, p. 478 - 481
  • 28
  • [ 1450-74-4 ]
  • [ 1423715-09-6 ]
YieldReaction ConditionsOperation in experiment
16 mg With acetic acid In methanol at 120℃; for 0.5 h; Microwave irradiation 1-(5-Chloro-2-hydroxyphenyl)ethanone (20 mg, 0.117 mmol) and 3- (morpholinosulfonyl) benzohydrazide (33.5 mg, 0.117 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120 °C for 30 min. Following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2percent CH3OH/CH2CI2) affording the title compound (16 mg) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.26 (m, 1 H), 8.17 (d, 1 H, J = 8.0Hz), 7.92 (d, 1 H, J = 8.0 Hz), 7.72 (t, 1 H, J = 8.0 Hz), 7.48 (d, 1 H, J = 2.0 Hz), 7.22 (m, 1 H), 6.91 (d, 1 H, J = 8.8 Hz), 3.72 (m, 4H), 3.01 (m, 4H), 2.43 (s, 3H). ESI-MS: 438.1 [M+H]+
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9496 - 9508
[2] Patent: WO2013/25805, 2013, A1, . Location in patent: Page/Page column 86; 87
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