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[ CAS No. 1877-75-4 ]

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Chemical Structure| 1877-75-4
Chemical Structure| 1877-75-4
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Product Details of [ 1877-75-4 ]

CAS No. :1877-75-4 MDL No. :MFCD00014360
Formula : C9H10O4 Boiling Point : 328°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :182.17 g/mol Pubchem ID :74649
Synonyms :

Safety of [ 1877-75-4 ]

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 [ 1877-75-4 ]

  • Upstream synthesis route of [ 1877-75-4 ]
  • Downstream synthetic route of [ 1877-75-4 ]

[ 1877-75-4 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1877-75-4 ]
  • [ 39581-55-0 ]
YieldReaction ConditionsOperation in experiment
10% at 75℃; for 0.833333 h; In an 1 I-three-necked flask with a drying pipe, KPG stirrer and glass stopper, 310 g polyphosphoric acid (84percent; Across Organics) were weighed in and were heated at an oil bath temperature of 75°C. Within 10 min 8.6 g (47.15 mmol) (4- methoxyphenoxy) acetic acid were added; then stirring was carried out for 40 min at 75°C. The cooled solution was poured onto 1.5 1 ice. After stirring during 2 hours, three extractions were carried out with a total of 400 mi chloroform. The combined organic phases were washed with water, 10percent K2CO3 solution and again with water and were dried over Na2SO4. After removal of the solvent in the rotation evaporator, the residue was purified by column chromatography (silica gel 60; chloroform). Thus, 774 mg (10percent) 5-methoxy-3(2H)-benzofuranone were obtained. For an alternative formula, cf. Hammond et al. ; 1990 [29].
Reference: [1] Patent: WO2003/93258, 2003, A2, . Location in patent: Page/Page column 18
  • 2
  • [ 150-76-5 ]
  • [ 79-11-8 ]
  • [ 1877-75-4 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With sodium hydroxide In waterCooling with ice
Stage #2: for 0.333333 h;
Stage #3: at 105℃; for 5 h;
General procedure: Compounds B1−7 were prepared by similar procedures. In atypical synthesis of B1, monochloroacetic acid (0.04 mol,3.78 g) was dissolved in deionized water (15 mL) under thecondition of stirring and an ice bath. Then NaOH (25 percent) wasadded dropwise until the pH value was adjusted to 9−10, thena solution of sodium chloroacetate was obtained. To a solutionof NaOH (0.03 mol, 1.20 g), deionized water (15 mL) andethanol (5 mL), phenol (0.04 mol, 3.76 g) was slowly addedunder stirring. After addition, the mixture was stirred for20 min, then the above sodium chloroacetate was addeddropwise, and heated to 105 °C and refluxed for 5 h. Thereaction mixture was cooled to room temperature. The pHvalue of the mixture was acidified to 1−2 with diluted hydrochloricacid. The precipitate was filtered, washed with dilutedhydrochloric acid many times, and recrystallized and dried invacuum, resulting in a white solid product of thephenoxyacetic acid (B1)
68%
Stage #2: With sodium hydroxide In ethanol; water at 105℃; for 5 h;
General procedure: A mixture of NaOH (0.04 mol, 1.60 g), deionized water (20 mL) and ethanol (20 mL) were poured into a 150 mL three-necked flask, then phenol (0.04 mol, 3.76 g) was slowly added under stirring.
Twenty minutes later, the above sodium chloroacetate was added dropwise.
The reaction solution was heated to 105 °C and refluxed for 5 h.
After cooling down, the pH value of the mixture was acidified to 1-2 with diluted hydrochloric acid.
The precipitate was collected by filtration and washed with diluted hydrochloric acid many times.
Recrystallized and dried under a vacuum, resulting in a white solid product of the phenoxyacetic acid (4a).
Reference: [1] Synthetic Communications, 1996, vol. 26, # 23, p. 4337 - 4341
[2] Journal of Fluorescence, 2015, vol. 25, # 4, p. 849 - 859
[3] Luminescence, 2018, vol. 33, # 5, p. 855 - 862
[4] Luminescence, 2015, vol. 30, # 5, p. 677 - 685
[5] Journal of Molecular Structure, 2014, vol. 1074, p. 487 - 495
[6] Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 135 - 137
[7] Tetrahedron, 2004, vol. 60, # 46 SPEC. ISS., p. 10469 - 10477
[8] Journal of the American Chemical Society, 1931, vol. 53, p. 304
[9] Journal of the American Chemical Society, 1943, vol. 65, p. 1555
[10] Chimica Therapeutica, 1970, vol. 5, p. 211 - 215
[11] Agricultural and Biological Chemistry, 1983, vol. 47, # 11, p. 2653 - 2656
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4597 - 4601
[13] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4726 - 4733
[14] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 12, p. 3180 - 3186
[15] Phosphorus, Sulfur and Silicon and the Related Elements, 2014, vol. 189, # 9, p. 1337 - 1345
[16] Research on Chemical Intermediates, 2016, vol. 42, # 6, p. 5269 - 5280
[17] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187
[18] Patent: CN103666452, 2016, B, . Location in patent: Paragraph 0076; 0077
  • 3
  • [ 3926-62-3 ]
  • [ 150-76-5 ]
  • [ 1877-75-4 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With sodium hydroxide In ethanol; water at 20℃; for 0.333333 h;
Stage #2: at 102℃; for 5 h;
General procedure: 55mmol monochloroacetic acid was dissolved in 15mL deionized water under the condition of ice water bath, then 30percent NaOH solution was used to adjust pH 8–9, sodium chloroacetate solution was obtained. 45mmol NaOH was dissolved in mixed solvent of 15mL deionized water and 5mL ethanol at room temperature with constant stirring, 45mmol phenol was subsequent slowly added. After stirring for another 20min, sodium chloroacetate solution was added. Subsequently, the mixture was refluxed at 102°C for 5h. After the mixture was cooled to room temperature, pH was adjusted to 1–2 with 2.0mol·L−1 HCl, amounts of white precipitations were gained. The precipitations were filtered and washed 3 times with dilute hydrochloric acid, dried at 60°C. White crude product was dispersed in 100mL heated deionized water, pH was adjusted to 8.0 using saturated potassium carbonate solution, then mixture solution was filtered, and filtrate was collected. White precipitated was obtained by adjusting pH of filtrate to 1–2 with 2.0mol·L−1 HCl. After cooled down to room temperature naturally, the mixture was filtered, washed with dilute hydrochloric acid, dried overnight in vacuum, then target product (b1) was obtained. The synthetic procedures of phenoxyacetic acid derivative (b2−7) were similar to that of phenoxyacetic acid (b1).
Reference: [1] Medicinal Chemistry Research, 2010, vol. 19, # 1, p. 33 - 57
[2] Dyes and Pigments, 2018, vol. 158, p. 28 - 35
[3] Luminescence, 2014, vol. 29, # 8, p. 1113 - 1122
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  • [ 18598-23-7 ]
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Reference: [1] Journal of Materials Chemistry, 1998, vol. 8, # 4, p. 919 - 924
[2] Journal of the American Chemical Society, 1987, vol. 109, p. 5235
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 23, p. 10049 - 10060
[4] British Journal of Pharmacology, 2013, vol. 170, # 4, p. 822 - 834
[5] Patent: WO2014/100730, 2014, A1, . Location in patent: Paragraph 00270
[6] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530
  • 5
  • [ 150-76-5 ]
  • [ 1877-75-4 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 5235
[2] British Journal of Pharmacology, 2013, vol. 170, # 4, p. 822 - 834
[3] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5492 - 5500
[4] Patent: WO2014/100730, 2014, A1,
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735
[6] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5601 - 5603
[7] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530
  • 6
  • [ 22446-17-9 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5601 - 5603
  • 7
  • [ 79704-02-2 ]
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 2, p. 154 - 156
[2] Journal of Chemical Research, 2010, # 8, p. 452 - 454
[3] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5492 - 5500
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735
  • 8
  • [ 96-34-4 ]
  • [ 150-76-5 ]
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4458 - 4465
  • 9
  • [ 79-08-3 ]
  • [ 150-76-5 ]
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Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 9, p. 1506 - 1511
[2] International Journal of Chemical Kinetics, 2001, vol. 33, # 10, p. 612 - 616
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4458 - 4465
  • 11
  • [ 111479-08-4 ]
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4458 - 4465
  • 12
  • [ 105-36-2 ]
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  • [ 1877-75-4 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 47, p. 8986 - 8993
  • 13
  • [ 2211-94-1 ]
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  • [ 150-76-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 16, p. 2601 - 2604
  • 14
  • [ 1122-95-8 ]
  • [ 3926-62-3 ]
  • [ 1877-75-4 ]
Reference: [1] Zhurnal Analiticheskoi Khimii, 1950, vol. 5, p. 7,8[2] Chem.Abstr., 1950, p. 4374
[3] Doklady Akademii Nauk SSSR, 1949, vol. 68, p. 77,79[4] Chem.Abstr., 1950, p. 1936
  • 15
  • [ 1122-95-8 ]
  • [ 79-11-8 ]
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Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 333 - 338
  • 16
  • [ 64-17-5 ]
  • [ 623-11-0 ]
  • [ 815627-04-4 ]
  • [ 586-96-9 ]
  • [ 93-98-1 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1937, vol. <2> 148, p. 126,133
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  • [ 623-11-0 ]
  • [ 815627-04-4 ]
  • [ 138-89-6 ]
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  • [ 889-38-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1937, vol. <2> 148, p. 126,133
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