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[ CAS No. 39581-55-0 ]

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Chemical Structure| 39581-55-0
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CAS No. :39581-55-0 MDL No. :MFCD08544410
Formula : C9H8O3 Boiling Point : 299.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :164.16 g/mol Pubchem ID :346608
Synonyms :

Safety of [ 39581-55-0 ]

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
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  • Upstream synthesis route of [ 39581-55-0 ]
  • Downstream synthetic route of [ 39581-55-0 ]

[ 39581-55-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 75717-53-2 ]
  • [ 39581-55-0 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium acetate In ethanol for 1 h; Heating / reflux
Stage #2: With hydrogenchloride In ethanol; water
To an ice-cooled solution of boron trichloride (1.2 equiv., 10 mmol, 10 ml of a solution of 1M BC13 in dichloromethane) under N2-atmosphere was added dropwise a solution of J (1 g, 8 mmol,) in dichloromethane (5 ml). Then, chloroacetonitrile (0.7 g, 10 mmol, 1.2 equiv. ) was added dropwise, followed by aluminum(III) chloride (0.5 g, 4 mmol, 0.5 equiv. ) in one portion. The reaction mixture was allowed to warm up to room temperature and was stirred for 6 h. The reaction mixture was diluted with dichloromethane and quenched with IN hydrochloric acid at 0°C. After stirring for 10 min, the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried (MgS04) and concentrated Purification by flash chromatography on silica gel (eluent: dichloromethane) afforded the desired product K [Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N.; Jensen, Norman P.; McDonald, John; Thompson, Kathryn; Boulton, David A.; Kopka, Ihor E.; Hand, Karen M. Journal of Medicinal Chemistry 1990,33(3), 908-18] (1 g, yield = 60percent). Intermediate K (0.15 g, 0.75 mmol, I equiv. ) and potassium acetate (0.22 g, 2.2 mmol, 3 equiv. ) were refluxed in ethanol (10 ml) for 1 h. After cooling, the reaction mixture was filtered and concentrated. The residue was mixed with water, and acidified with IN hydrochloric acid to pH = 1. The aqueous solution was extracted with ethyl acetate, the combined extracts were dried (MgS04), filtered and concentrated to afford the desired product L [Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N. ; Jensen, Norman P. ; McDonald, John; Thompson, Kathryn; Boulton, David A.; Kopka, Ihor E.; Hand, Karen M. Journal of Medicinal Chemistry 1990, 33(3), 908-18] (110 mg, yield = 90 percent) as a pink solid The experimental procedures for the condensation reaction of compound L with 4-nitroaniline in acetic acid to form compound M, followed by Vilsmeier-Haack formulation and subsequent Knoevenagel condensation of the benzofuran carbaldehyde N with ethyl cyanoacetate to form compound 0, and finally, intramolecular cyclisation to compound 37 were performed using analogous procedures as exemplified in example 1 for the synthesis of compound f starting from compound a. Compound 37 was obtained as a yellow powder (30 mg, purity (LC) = 80 percent).
86.8% With sodium acetate In ethanol for 2 h; Reflux Compound 3 (3.8 g, 18.9 mmol) was dissolved in ethanol (50.0 mL),Sodium acetate (3.3 g, 39.8 mmol) was added with stirring and refluxed for 2 h.After concentration, add water, extract with dichloromethane (80 mL×3), combine the organic layers, and wash.Saturated brine wash, dry anhydrous Na2SO4,Column chromatography after concentration (PE/EA 15:1, v/v) gave the target compound 4 (2.7 g, 86.8percent).
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 12, p. 5950 - 5957
[2] Patent: WO2005/111035, 2005, A1, . Location in patent: Page/Page column 78-79
[3] Patent: CN107365322, 2017, A, . Location in patent: Paragraph 0098; 0102
[4] Organic Letters, 2008, vol. 10, # 4, p. 573 - 576
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918
[6] Patent: WO2015/95261, 2015, A1, . Location in patent: Page/Page column 96
[7] Patent: WO2015/89842, 2015, A1, . Location in patent: Page/Page column 95
[8] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
  • 2
  • [ 60770-20-9 ]
  • [ 39581-55-0 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 150℃; for 4 h;
Stage #2: for 2 h; Heating / reflux
Step 3: The 2-(carboxymethoxy)-5-methoxy-benzoic acid compound obtained from the step 2 (11.3 g, 50 mmol) was dissolved in acetic anhydride (100 ml) and anhydrous sodium acetate (10.0 g, excess) was added. The reaction mixture was heated to 150° C. for 4 hrs. During this time the reaction mixture turned dark red. The reaction mixture was cooled to room temperature and quenched carefully with ice cold water. The red solid obtained was filtered and washed well with water. The red solid obtained was suspended in 1 N HCl and refluxed for 2 hrs. A dark red solid, 5-methoxy-benzofuran-3(2H)-one, precipitated from the reaction mixture. It was filtered and washed well with water. It was dried at 40° C. and used for the next step without further purification. Yield: 6.2 g (75percent); (M+H): 165.
75%
Stage #1: at 150℃; for 4 h;
Stage #2: With hydrogenchloride In water for 2 h; Heating / reflux
The 2- (carboxymetlioxy)-5-methoxy-benzoic acid compound obtained from the step 2 (11.3 g, 50 mmol) was dissolved in acetic anhydride (100 ml) and anhydrous sodium acetate (10.0 g, excess) was added. The reaction mixture was heated to 150 C for 4 hrs. During this time the reaction mixture turned dark red. The reaction mixture was cooled to room temperature and quenched carefully with ice cold water. The red solid obtained was filtered and washed well with water. The red solid obtained was suspended in 1 N HC1 and refluxed for 2 hrs. A dark red solid, 5-methoxy-benzofuran-3 (2H) -one, precipitated from the reaction mixture. It was filtered and washed well with water. It was dried at 40 C and used for the next step without further purification. Yield: 6.2 g (75percent); (M+H) : 165.
Reference: [1] Patent: US2009/54454, 2009, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2004/99191, 2004, A2, . Location in patent: Page 62
[3] Patent: US2005/4162, 2005, A1, . Location in patent: Page/Page column 17
  • 3
  • [ 107-14-2 ]
  • [ 150-76-5 ]
  • [ 39581-55-0 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogenchloride In 1,1-dichloroethane; water at 0 - 35℃; for 3.5 h;
Stage #2: With sodium acetate In methanol for 1.5 h; Heating / reflux
Reference example 1; General procedure for obtaining benzofuranones III; A solution of 48.3 ml_ of 1 N BCI is cooled in an ice bath. A solution of 5 g (40.3 mmol) of 4-methoxyphenol in 100 ml_ of dichloroethane is added slowly to this solution at O0C for 1 h. A solution of 3.06 ml_ (48.3 mmol) of chloroacetonitrile in 10 ml_ of dichloroethane is added. 2.69 g (20.14 mmol) of AICI3 are added in portions such that the temperature never exceeds 350C. Stirring is continued at O0C for 2.5 h. Once the reaction has finished, the crude product is poured over a suspension of ice and 1 N HCI. The phases are separated. The aqueous phase is extracted with 30 ml_ of dichloroethane. The organic extracts are gathered and dried over anhydrous magnesium sulphate. <n="14"/>The solvent is filtered and eliminated under low pressure. The residue thus obtained is redissolved in 100 ml_ of MeOH. 9.91 g (121 mmol) of sodium acetate are added at once and the mixture is boiled for 1 h and 30 min. It is allowed to cool and filtered. The filtrate is extracted with dichloromethane (DCM) and 1 N NaOH. Dry, filter and evaporate the organic phase. 4.07 g (Yield = 55percent) of the benzofuranone III are obtained as a yellowish oil.HPLC-MS: Purity 99percent, M+1 = 165
30%
Stage #1: With boron trichloride In n-heptane; dichloromethane; 1,2-dichloro-ethane at 0℃;
Stage #2: at 0 - 20℃;
Stage #3: With sodium acetate In methanolReflux
Benzofuranone 19 was prepared from 4—methoxyphenol according to literature procedure (Hammond, M.L. et al. 1990) and obtained as orange—tan crystals (2.49 g, 30percent).
Reference: [1] Patent: WO2009/53444, 2009, A1, . Location in patent: Page/Page column 12-13
[2] Patent: WO2016/86158, 2016, A1, . Location in patent: Page/Page column 97; 99
  • 4
  • [ 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
  • 5
  • [ 60770-33-4 ]
  • [ 39581-55-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5743 - 5748
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6354 - 6363
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 824 - 827
  • 6
  • [ 150-76-5 ]
  • [ 39581-55-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918
[2] Patent: WO2015/95261, 2015, A1,
[3] Patent: WO2015/89842, 2015, A1,
[4] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
[5] Patent: WO2005/111035, 2005, A1,
  • 7
  • [ 203524-87-2 ]
  • [ 39581-55-0 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 1, p. 17 - 20
  • 8
  • [ 17918-14-8 ]
  • [ 39581-55-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2134 - 2145
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 11, p. 2061 - 2064
  • 9
  • [ 2785-98-0 ]
  • [ 39581-55-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2134 - 2145
  • 10
  • [ 150-78-7 ]
  • [ 39581-55-0 ]
Reference: [1] Patent: CN107365322, 2017, A,
  • 11
  • [ 1204-22-4 ]
  • [ 39581-55-0 ]
Reference: [1] Patent: CN107365322, 2017, A,
  • 12
  • [ 39581-55-0 ]
  • [ 13196-10-6 ]
Reference: [1] Patent: WO2015/95261, 2015, A1,
[2] Patent: WO2015/89842, 2015, A1,
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